The Observer's Notebook: Volume I

216 Lessons Learned Over 17 Months | June 7, 2023 - November 7, 2024

Photo by Thomas Martinsen on Unsplash

6/7/23

1.      Valuation is stressful for founders. 💵

Founders (at least, the ones I talk to) hate the process of negotiating a valuation. I was speaking to one this week, and he summarized the general sentiment well when he said “it feels extremely arbitrary, it’s driven by market sentiment, and there are so many methods that I have no idea where to start.”

2.      Access = value. 🎸🎮

Access to an experience is valuable and is something I’m thinking about this week as we create and iterate. Two of my personal experiences from the week brought focus to this concept:
#1: On Thursday my wife Dani and I went to an All Time Low concert at the Moody Center in Austin. It was a blast. She’s a concert junkie, so we happily paid extra to be on the floor. But there was a small group of superfans who got to enjoy the concert from the side of the stage - my guess is they paid 3x what we did for that backstage access.

#2: Blizzard’s latest title, Diablo IV, was released yesterday. I had some downtime over the weekend and was surprised how tempted I was to spend the extra $20 to purchase the “deluxe” edition, which provided access to the game several days before the full release.

3.      Inefficiency = Opportunity. 🗣️

Most angel networks we’ve spoken to have mentioned at some point how difficult it is to give good, consistent feedback to founders. Most founders we’ve spoken to have mentioned at some point how disappointing it is when they don’t receive good feedback from angels because they’re left confused and unsure of where they went wrong. Well, since we’ve now analyzed 200 companies, we figured this is something we could help founders with - an opportunity💡. So this week we kicked off an alpha run for a new service offered exclusively to founders referred by our existing clients. It’s pretty simple - we basically run the founder through a “practice run” of the entire Angel Ops process and give them thorough feedback at each step. This includes an evaluation of the strength of their application, screening interview, pitch, deep dive diligence & data room, and follow-up plan. Exciting times!

6/14/2023

4.      Applications suck. 📝

This week I finally did it. I gritted my teeth for 11.7 hours and I did it. I personally went through every single question asked by 12 different angel networks in their online application to pitch. To make one mega application. We call it “The Beast”. Besides learning what it’s like to hear fingernails scraping against a chalkboard for 1.5 working days, here are some other takeaways:

a.      Angel network applications are all basically asking the same stuff, but there are slight variations from network to network that make it extremely time-consuming for a founder to complete.

b.      It was really nice when a network provided a thorough overview of the process, fees, and what to expect at the very beginning. Most didn’t.

c.      Applications suck.

5.      Small wins are emotional lifelines. 🛟

This month, we closed 2 small deals, and we’re beyond pumped. I’m sure every founder who has found “product-market fit” has a journey that is littered with “stuff that didn’t work out,” and maybe it’s obvious to everyone else, but as my team and I live out the journey personally I’ve been shocked at how much willpower it takes to keep doing new stuff knowing that it probably won’t pan out as we expect. Every week we learn a little more, and that forces us to change our approach and try something new, but it’s tough. So securing small wins is invigorating for the whole team - it creates this ethos of “wow we found something that works!” and that’s enough to keep us going.

6.      Magic trick: paying someone to do a thing forces you to make a call. 🪄

Our team has talked at length about one stupid survey at least 6 different times this quarter. And we never landed on exactly what we wanted it to look like. Maybe that’s due to my shortcomings at driving us to a decision (I’m growing!), but this week I figured out a cool trick to help. We recently started working with Clay Moss, an experienced UI/UX designer, to refresh our website (highly recommend). He’s been working with us at length over the last few weeks, and the next item in his hopper was this particular survey. Of course, we could have just had him design it 10 different ways and kick the can down the road again, but the bootstrapping mindset doesn’t look kindly on that approach. So we forced ourselves to set a meeting, take an hour, and (finally) make some decisions. And we did. Magic.

6/21/23

7.      On good teams, being the first to propose a thing is hard. 🌪️

This week, our CTO TJ Daly made a passing comment that stuck with me. He said, “You know, I always feel a little bad for whoever is the first to come up with a new idea or product because they spend a lot of time working on it and then we just rip it apart when they present.” It’s true. I’m not always the one in that seat, but as the sales lead and designated “ideas guy” I tend to find myself often presenting crazy new things. But I believe that the “robust dialogue” consistently present in our team meetings is one of the surest signs of health. PitchFact team meetings are definitely not boring…

8.      Sometimes what customers ask for is not what they need. 🦲

I’ve been developing a proposal this week, and I think it’s going to blow the prospect’s mind. Why? Because I’ve spent a long time listening, learning, and thinking about their needs, their process, and how we are uniquely positioned to help. Without going into detail, the proposal addresses what they asked for, but in a way that simultaneously addresses a host of other known issues. Thanks to some well-placed feedback from our team (see learning #1) we’ll also be quoting the bare minimum of what they asked for, but I realized through this process that sometimes a prospect doesn’t actually know how to ask for what they need, and it’s part of our job to help them out.

9.      Time is precious. ⌛

I’ve recently been reflecting on the value of time. This week I stumbled across this fascinating chart from Our World in Data that shows the progression of who we spend our time with over the years, and it’s blowing my mind.

Here are 3 of my personal takeaways:

#1: Time alone trends upward over our whole lives. Learn to enjoy yourself.
#2: Time with friends and family flatlines by age 30. Treasure it.
#3: Time with partner trends upwards over time. Choose wisely.

6/28/23

10.   Life is a gift.🏠🎁

On Sunday, our house’s AC system super died. I spent most of the day attempting to fix it before giving up and calling in the pros, who confirmed we had a critical failure. Thankfully some local friends have generously opened their home to us while we work out the fix (you know it’s a bad day when it feels better outside the house than inside. And it’s 100 degrees outside…). As I’ve processed the last few days and the impact of an unplanned 5 figure expense, I’ve been surprised to discover that my primary takeaway (besides exhaustion) has been this: life is a gift. Nothing is certain, I’m not in control, and all I can do is choose to be grateful for what I have. Take nothing for granted.

11.   Events are a great investment. 📅

In this week’s quarterly review, we spent some time reflecting on what worked and what didn’t from 23Q2. One of the things we realized was particularly effective for us was attending events. Why? We think it’s because they create a natural platform for forming real relationships. Expect to see us around a bit more often this quarter…

12.   Good character is good for business. 💼

This week I started reading Return On Character: The Real Reason Leaders and Their Companies Win by Fred Kiel (this was, admittedly, before the AC quit). It was a recommendation from Mike Elliot, who I had the pleasure of meeting a couple of months ago at Lions Den DFW (a faith-based & impact-driven pitch competition hosted by Dallas Baptist University). In the book, Kiel summarizes research findings from his company’s thorough character study of 121 CEOs in the US. If you don’t have time to pick up the whole book, here is an HBR summary of the research.

7/5/23

13.   Clients don’t need to like you to be happy with you.🙂

On Thursday we (finally) got our AC up and running. However, the process of getting there was pretty stressful since we needed a major replacement. I contacted a half dozen contractors to compare options (I do run a diligence company after all), and every one of them was professional, helpful, polite, and had the capacity to get us up and running within 24hr. Except one. One local contractor was a bit more challenging to work with. He wasn’t in a rush to get back to me. He was borderline rude over the phone. His lead times were longer than the others. But his pricing was reasonable, and he took the time to explain to me, in detail, why I did not need the “full system replacement” that all the others were pushing me towards. This 50-something HVAC pro was downright unpleasant, but guess who I decided to trust with my family’s home? Lesson learned: clients don’t have to like you, they just need to trust you. (If anyone with property in the Brazos Valley needs an HVAC referral, let me know!)

14.   A sample’s worth a thousand words. 📃

This week I spent some time consolidating representative samples of a few types of diligence reports we’ve created so far. A recent acquaintance, who I’ve had the pleasure of speaking with on a few occasions now, asked for these off-hand following our latest meeting. Within 1 business day of sharing, I found myself on an impromptu video call with him answering a barrage of questions and excitedly ideating together on what future collaboration might look like. Lesson learned: samples are super helpful for bringing things down to earth.

15.   Talking to customers about your thing is a really good idea. 📞

We’ve been ideating for weeks on a stripped-down version of our Premium Pitch Report (a 6-page overview of a startup’s market, traction, opportunity, and team, generally most useful during Stage 3 - Engage). We had developed a decent prototype of what we thought would be compelling and were pretty confident about it. This week we (finally) showed it to a client. Guess what? They gave us incredibly helpful feedback and I spent most of Friday totally reworking the product. Lesson learned: talk to customers early and often.

7/12/23

16.   Calm control is the mark of an expert.🧗

After months of peer pressure, this week I finally caved and signed up for a membership at our local climbing gym. When climbing with a friend of mine who is much more advanced, I noticed the way he moved on the wall and the way I moved were starkly different. I climb a route kind of like a beached walrus - usually flopping around trying to brute force my way through. But he moves with intentionality, grace, and control that reflects years of training and hard work. It’s impressive to behold, and the concept translates to any other skill.

17.   Numbering your days is humbling.⌛

This week I lived my 10,000th day. According to a recent CDC report, the average life expectancy in the US is 76.1 years. That works out to about 28,000 days. I obviously have no idea what tomorrow holds, but assuming I’m “average” and live exactly that long, that means I’ve experienced 36% of life. To mark the occasion, I spent some dedicated time reflecting on where I’ve been, where I am, and where I hope to go. I started keeping track years ago after reading Psalm 90:12, which says “Teach us to number our days, that we may gain a heart of wisdom,” and have found the practice to be deeply humbling.

18.   They made a trust equation. 🤝

I love simple frameworks, and this week I found one for trust. It’s qualitative, similar to the motivation equation I introduced a few weeks ago, and boils down to (Credibility + Reliability + Authenticity) / Perceived Self Interest. I stumbled across this long but helpful article breaking it down from First Review (credit to Lenny Rachitsky from his latest podcast episode), which draws from The Trust Equation by Steven Drozdeck and Lyn Fisher.

7/19/23

19.   Chinese weddings have the coolest traditions.🧧

This weekend I got to attend my first Chinese wedding, and one tradition in particular stood out to me: the Tea Ceremony. It was held the evening before, and after enjoying WAY too much food, the bride and groom invited a procession of family elders (grandparents, parents, aunts/uncles, and others) to the front. The couple got down on their knees together and served each elder a cup of tea, after which the elder would offer advice and a gift (the famed red envelope!). I was impressed by the symbolism of the event, and after a few years of marriage found myself appreciating a lot of the advice that was shared.

20.   Vetrepreneurs lean in.🎖️

One of our company’s core values is “Lean In.” This week, I saw that value on display in a powerful way. On Friday I was given the opportunity to speak with a group of veteran entrepreneurs at the Reynolds and Reynolds Entrepreneurship Bootcamp for Veterans Reunion hosted by the McFerrin Center for Entrepreneurship. Not only had every one of these men and women served in our country’s armed forces, but many of them have been leading businesses for 20 years or more. Despite the fact that I’m a civilian less than a year into my own entrepreneurial journey, they were humble enough to listen to me for an hour, ask excellent questions, and engage in a way that left me excited to come back. And they even sent me away with a thoughtful gift.

21.   Real deadlines are amazing motivators.📆

This week we turned in 3 Pitch Reports (fairly in-depth 6-page overview of a company’s market, traction, opportunity, and team) for a client’s event, PLUS a completely reworked web application for distributing information to and engaging with members. It was a scramble the week before to get everything built, tested, and rolled out in time, but we did it, and I’m reminded yet again how helpful it is for “getting stuff done” to have real deadlines (as opposed to self-imposed deadlines).

7/26/23

22.   Life can change pretty fast.⏩

This week I had the opportunity to reconnect with 3 classmates from business school. We graduated 8 months ago. None of them are doing what they thought they’d be doing at graduation.

23.   Custom research is a lot of work. 🔨

This week we wrapped up the first draft of a fairly thorough analysis of several specific markets within the nonprofit space. It’s been an excellent project, but it has taken twice as much work as we thought it would. Lesson learned: next time we take on custom research I’ll 3x the amount of time spent developing the upfront scope, will protect that scope fiercely, and will price to allow a bit more breathing room.

24.   Communicating the essence of a business in 60s or less is very hard. 📬

This week I had the honor of hearing two dozen veteran entrepreneurs pitch their businesses in 60 seconds or less. I was reminded how hard that is to do and was impressed with how many were able to get it done in time. It’s easy to forget how much work founders put into consolidating and condensing their messaging, so this was a great reminder of one of my favorite sayings: “If I had more time, I would have written a shorter letter.”

8/2/23

25.   Terminology Matters.🧐

This week, TJ and I attended a virtual workshop hosted by the City of Austin and led by Paul O’Brien, CEO of MediaTech Ventures. During the presentation, Paul took great pains to define his terms. He stated that one of the biggest problems with the early-stage investing ecosystem is that we often use the same terms to mean different things, which creates major confusion for founders everywhere. I couldn’t agree more.

26.   The music industry has a lot in common with Venture Capital.📀

This week, Dani and I drove to Denver (about 14hrs). Naturally, we had to listen to at least 1 long-form business podcast, but our compromise was that she got to pick the episode. So we listened to The Acquired Podcast episode on Taylor Swift, which I highly recommend. Some reasons: record labels take risks on many early-stage artists who are not yet proven and rely on winners to carry their returns, 1% of musicians earn 77% of recorded music income, and record label advances have some similar features to a venture investment (very interesting breakdown from Alex Danco on the term sheet similarities and difference here).

27.   Three things that hiking my first Class 3 14er taught me about business.🏕️

On Sunday, Dani and I hiked Torrey’s Peak, which is a 14,272 ft mountain located about an hour west of Denver. There were a few routes available, but we chose to take the Kelso Ridge route, which is considered a Class 3 difficulty climb. Here are 3 things I learned:

a.      Plan ahead and start early.

We checked the weather the night before, and a storm was projected for early afternoon. So we started our hike at 4:30 am and finished by noon. On our return trip from the peak, we came across dozens of late starters, who apparently did not check the weather. A storm rolled in right as we drove away from the trailhead.

b.      Acknowledge your limits.

It’s a lot harder to breathe at 14,000 ft than it is at 289 (College Station’s elevation). During the strenuous climb, we had to take lots of breaks to catch our breath. Failure to do so could have led to injury or death.

c.      Community inspires.

At the most difficult point of the climb, where we were literally scrambling with our hands and feet on a knife’s edge at 13,000ft+, we ran into another group of climbers. Despite having never met these people before, we all cheered each other on, made jokes, and shared tips as we went. Dani told me afterward “I wasn’t sure if I would be able to make it at first, but meeting those other climbers inspired me, and I knew I could do it.”

8/9/23

28.   🙅‍♂️Strategy is as much about defining what not to do as what to do.

In B-School, we took an entire course called “Business Strategy”. In it, we studied writing from strategic thinkers like Michal Porter, Clayton Christensen, and more. We reviewed dozens of case studies, put ourselves in the shoes of business decision-makers throughout history, and analyzed the outcomes of the actual decisions that were made. This week, as I listened to an episode of Invest Like the Best where Rebecca Lynn, who founded Canvas Ventures, spoke with Patrick O’Shaughnessy, I was struck by a question she likes to ask founders: “How many potential customers have you said no to?” Maintaining focus is very difficult when you’re like me and get easily distracted by shiny new things. 

29.   🔍Know the facts.

This week I read “Ogilvy On Advertising” by David Ogilvy (1911 - 1999), who was an advertising legend during the mid-20^th century. I learned about the book thanks to a very practical podcast episode from David Senra, which I highly recommend. It’s chock full of timeless advice and examples, but one of the things that stuck out to me was his obsession with making advertising decisions based on what does and does not deliver results. He quotes the Benton & Bowles agency’s belief that “if it doesn’t sell, it isn’t creative,” and clearly relies upon this throughout his career. In the book, he relentlessly cites studies, surveys, and performance data for every factor imaginable. Here are three examples that stood out to me on the topic of headlines alone:

a.      “…advertisements with headlines that promises a benefit are read by an average of four time more people than advertisements that don’t.”

b.      “On average, five times as many people read the headline as read the body copy.”

c.      “When you put your headline in quotes, you increase recall by an average of 28%.”

30.   🔄🔄Two iterations make stuff exponentially better.

This might seem obvious, but most first drafts suck. Even if I think something I’ve made is great, our team has consistently found that by submitting things for review and taking at least 2 passes at the document, deliverable, proposal, plan, etc, the final product comes out exponentially better. It takes a lot of time, but one of our company values is “Highest Standard”, and we’ve naturally evolved into a culture of expecting at least 2 iterations and feedback loops on important deliverables before calling them “done”.

8/16/23

31.   🎨Graphic designers are worth the money.

Last week, I held the position that our standard reports looked pretty good. This week, that opinion has completely changed. We finally hired a graphic designer to help us level up the look and feel for one of our reports. I now cringe when I look at our original designs because the new version is just exponentially better. Lesson learned: designers are worth the money.

32.   📋Editorial workflows are amazing.

This week, per our designer’s recommendation, I learned how to use Adobe InDesign and InCopy. I had no idea this software existed before, but the suite includes some crazy helpful editorial workflows. For example, over the last few days, I created templates for each of our 3 primary styles of reports. I specified certain sections as “editable” and others as “fixed.” Now anytime we create a new report, I can generate “assignments” that allow an analyst to work within strict boundaries and only on the copy I want them to be able to modify. Once they’ve finished loading their content, the designer can auto-populate the template with the analyst’s copy, review the design to make sure everything’s kosher, and publish. After creating dozens of reports over the last year, our team is very excited about this new workflow. It saves the analyst time worrying about formatting/editing while simultaneously ensuring visual quality and brand alignment.

33.   👍Microsoft has its own Notion competitor called Loops, and it’s pretty good.

Back in January, our team decided to go full Microsoft suite for business ops since we were all most familiar with that interface. So, love it or hate it, if you meet with me, it’ll be via Teams call. Anyway, this week I spent an hour setting up Microsoft Loop for our team. It’s got some pretty slick integrations and auto-updates across all platforms. There are definitely some improvements to be made, but I’m a fan and recommend giving it a shot if you’re a Teams user like me.

8/30/23

34.   Defining the market size for a thing is really hard.🧮

This week I noticed a common thread applicable to several clients. Market sizing is very hard. We’ve gotten pretty good at this and are seeing lots of interest. If you know of good resources for leveling up market analysis or know of someone really good at this, let me know, I’d love to see our team continue exploring and growing in this area.

35.   Getting people on the phone tends to reveal the real story. ☎️

I’ve recently been going back and forth with a prospective client for a few weeks regarding a “test drive” with one of our reports. We’ve rescheduled our meeting a few times since the ideal company for us to analyze hadn’t come up yet, but this week we just hopped on a call anyway to check-in. Wanna know what I learned? The real issue was less about the lack of opportunities to be researched and more about the fact that our “off-the-shelf” report didn’t quite fit the work he was looking for. Let’s just say it was a very productive phone call.

36.   It’s not about the price. It’s about the problem. 🧩

It is very easy to get wrapped up in and overly focused on the price we charge for our services. It’s something I’ve personally allocated a lot of time, research, and head space towards. In any business, the price of a thing is important. But at the same time, it’s really not. For example, this week I had a conversation with a client that basically didn’t care what the price for our stuff was. All he cared about was that we could help solve his problem, and as long as our fee was “not ridiculous,” he didn’t care what it was. It was a good reminder to focus first and foremost on figuring out a way to consistently solve a hard problem that enough people face and are willing to pay something to fix. The rest will fall into place.

9/6/23

37.   Infrastructure is very important. 🌉

This week I attended “Angel Investing in the Energy Sector” hosted by the Houston Angel Network at the Rice University campus. My biggest takeaway was that no matter how revolutionary it may be, new technology is impossible to commercialize if the fixed cost to deploy it exceeds the value it delivers.

38.   Invest in the good wrapping paper - it matters.🎁

This week we rolled out a total visual refresh of our flagship diligence report. We delivered 5 new reports for an event on Friday, and not only did I receive a half dozen separate in-person comments about how much people liked it, but the average report viewership and duration also increased relative to prior months. it was the same content as usual.

39.   Defining a clear strategy is hard, and takes more work than you’d think.🧠

I spent most of Labor Day working on our strategy. It was hard work and was made even harder by the LONG list of to-do list items I chose not to spend my time on. In that vein, I’m reading “Playing to Win: How Strategy Really Works” by A.G. Lafley and Roger Martin, and I’d like to share an excerpt that hit me right between the eyeballs:

“In short, strategy is choice. More specifically, strategy is an integrated set of choices that uniquely positions the firm in its industry so as to create sustainable advantage and superior value relative to the competition. Making choices is hard work, and it doesn’t always fit with all the other work to be done. In our view, far too few companies have a clear, choiceful, and compelling winning strategy in place. Too often, CEOs in particular will allow what is urgent to crowd out what is really important. When an organizational bias for action drives doing, often thinking falls by the wayside.”

9/13/23

40.   Clear communication is hard to learn, but essential to master. 📢

This week I overwhelmed our team. I did not communicate well. They entered a meeting to have a focused, tactical discussion, and I caught everyone off guard by taking it in a high-level strategic direction that was only semi-structured. I reprioritized in isolation without taking the time to explain why. Our time was not particularly well spent as a result, and everyone left disappointed. Lesson learned: Setting clear expectations for meetings ahead of time and presenting information in a well-structured format drives greater productivity. Yes it’s my job to set the vision and direction for the firm, but engaging our partners to develop collective buy-in and evolving based on our collective expertise is

41.   Talk to the founder ASAP. 🗨️

This week we were evaluating the market and competition for a client. We got started on the work just based on the deck we were provided, but after meeting with the founder to ask a few questions and hear more about their vision, we realized we were barking up the wrong tree. Meeting with the founder ASAP to really understand what they’re going for is a very good idea.

42.   Nobody cares about the what. All they care about is their problem: the why. 👊

I had one of those “I feel like I just got punched in the mouth” moments this week. I realized some of the language I’ve been using to describe our products and services to the world is product-focused rather than problem-focused. Why do clients hire us? To help them close or eliminate deals more effectively - not to write diligence reports or run a great process (though that’s what we do). Might be time for me to go re-read Simon Sinek’s “Start with Why.”

9/20/23

43.   The lobby >>>> the audience.🤝

Last week, I had a blast attending Dallas Startup Week. My favorite part of the event? Standing in the lobby. All. Day. Long. I admit I caught some of the content, which I enjoyed. But I continue to find that braving the awkwardness of walking up to a stranger and saying, “Hi, I’m Andrew. What’s your story?” is the most engaging, productive, and fun part of any event. Programming is great, but getting to know other interesting humans is ten times better. If you’re one of the dozens of new founders, investors, or other participants in the startup ecosystem who I met last week, thanks for saying hi.

44.   Talk less = sell more.🤐

Me: “Why don’t you like product X?” (referring to a tool we’re currently researching) Client: “I did. But when I met with the founder, I could never get a word in edgewise and was so put off by the sales approach that I never gave it a second look. If he had said less and just let me buy the thing, I might be a happy customer today.” Wow. Talk about validation for the “shut up and listen” sales approach.

45.   There’s a big difference between research and analysis.🔍 

One prospect’s process involves highly detailed preliminary research. The document they produce for each deal is dozens of pages long and very detailed. We’re scoping a single-page market analysis that will fit into their process after completing this preliminary research. When asked why they’re so interested despite our product’s concise nature, the response was, “sorting through all the data and focusing analysis on the most important things is hard to do well. That’s why we’re interested.”

9/27/23

46.   You never know what opportunity is going to come through the door.🕑

This week a hot project hit our desks through a friend of a friend. To be honest, we didn’t have the capacity to handle it, and we almost turned it down. But hey, I spent 4 years selling into oilfield production. What did I learn? If someone needs it now, they’ll pay whatever it costs to get it NOW. So you name a price and figure out how to make it happen. We did, and it paid off for all of us.

47.   Referrals are insane.🤯

This week I met with a connection who I was referred to by another acquaintance a few weeks ago. Neither of us had much context for the meeting, but after swapping introductions he said to me “If you know X and they went so far as to send you my way, I’ll do anything I can to help.” And he actually meant it - he volunteered to go the extra mile in several surprising ways after speaking with me for less than 30 minutes. Wild.

48.   Economics matter.📊

This week, I attended the Rice Alliance for Technology and Entrepreneurship Energy Tech Venture Forum in Houston. While there, I ran into a former Schlumberger executive who now runs a $1B+ fund at Saudi Aramco. I like to think I’ve seen a lot of pitches, but this guy has probably seen THOUSANDS, all concentrated in the energy world. So naturally, I asked him: “What’s one thing you look at in an energy deal that most founders miss on?” Here’s what he said: “The economics. Their financials are often built around the basic assumption that XYZ product will sell for $2,000 per ton, but how do we get to that price point? That material might sell for $750 on the market today, and many fail to think through the ramifications to their business if those price expectations are not grounded in reality.”

10/4/23

49.   Inventions require at least a 2-3x improvement to be commercially viable.🧪

This week I spoke with an inventor working on a new battery chemistry for the military, and I also spoke with a licensing manager about the process of working with large corporations to purchase and scale new inventions. It’s a complicated process, and the licensing manager mentioned that a 2-3x improvement over the status quo is typically a baseline requirement for a deal to get done.

50.   Humans are unpredictable.🤷‍♂️

This week one of our clients hosted their usual monthly pitch event. We recently implemented a “voting” system where their members can vote on which deals they’d like to see present. As a result, going into the meeting I felt very confident about which deals the members would be most interested in. I was completely wrong. Lesson learned: humans are unpredictable.

51.   A $12 book can deliver $100K+ in value if read at the right time.📖

PitchFact is growing. It’s a great problem to have, but a problem to solve nonetheless. Thanks to a friend’s recommendation, this week I read most of Who by Geoff Smart and Randy Street. It includes a simple and VERY helpful framework for hiring “A Players” consistently and repeatably. A few hours spent reading, digesting, and applying the concepts from this book left me feeling like I just saved my company from hundreds of thousands of dollars in hiring mistakes. I’d say the $12 and 2 hours I spent to buy and read the book was a fantastic investment.

Speaking of growth - who are the most talented people you know that I should hire?

10/11/23

52.   When the team is aligned decisions get made fast.⚡

“What’s important to us? What is our strategy? What is our vision? Why are we here?” Keeping the answers to these questions front and center with the team is essential to allowing quick decision-making. This week our executive team held our quarterly meeting, and we spent some time re-aligning around our mission and objectives. Two days later a client raised a question that we would have normally spent hours debating. But since we had just taken the time to get aligned around our objectives, it was a clean and simple decision to make.

53.   Money isn’t in the bank till it’s in the bank.🏦

This week I spoke with two founders who shared stories of investors who backed out at the last minute. They had, naturally, been *banking* on those financiers, and when the commitment dried up at the 11th hour, they both had to scramble to come up with a way to survive. It wasn’t pretty, and I was at a loss for how to help them. Lesson learned: always have a backup plan, especially when it comes to capitalizing your business.

54.   Know your value.💵

This week I was asked to consider taking on a significant project pro bono. Since we’ve already pre-defined the market price for each of the subcomponents within the project, it was very simple for me to do some “napkin math” and communicate the immensity of what was being requested. That was very helpful for redirecting the conversation and driving home the value of our work.

10/18/23

55.   “Don’t commit to a strategy while you’re still learning the rules of the game.”⚽

That is some wise advice I received this week that I am, in all honesty, wrestling with. I’ve devoted a lot of time and mental energy towards the goal of making early-stage startup diligence collaborative (that is, after all, part of our mission). I love the process of experimenting, trying new things, and failing fast. But sometimes my engineering training kicks in and I overthink things to a fault. Sometimes that tendency has been deeply helpful. In this case, I think it’s been a bit of both. Shoot me a note if you’re an experienced early-stage investor interested in learning more, I’d love to hear your take on what we’ve been working on.

56.   Giving an order is easy. Helping someone decide for themselves is hard.👮‍♂️

This week I had the opportunity to speak with a group of students at Startup Fast Pass on the topic of “How to Pitch.” After presenting, I spent some time bouncing from group to group to see how things were going. I was shocked at how common it was to hear students ask deterministic questions like “Should I do x or y?” I found it incredibly difficult to restrain myself from giving a binary order. However, since I believe the learning experience is far more effective when students are forced to think for themselves, I found myself re-teaching the same basic principles over and over again to help THEM decide which path was best.

57.   Pick a niche. Then pick a niche within that niche, and become the best.🔍

This week I had coffee with an experienced entrepreneur, investor, and executive. My main takeaway? Pick a niche and become the best. This is massively effective at establishing credibility and has been deployed again and again in his experience with great success.

10/25/23

58.   Be a valuable signal.📶

This week I was discussing the importance of sharing deal flow across angel groups with a network leadership team here in Texas. One of the things they said was “Deal flow is not a problem - quality deal flow is a problem. If you want to stand out as a valuable signal to the market, work to become a source of quality, not quantity.”

59.   Our answer to “What did you think?” is valuable.💭

I’m learning that clients consistently want to know what we think of an opportunity. Beyond the “official” analysis we produce, there’s interest in knowing what informally stuck out to us, what our impressions were, and why. It’s a good question to ask because we’re often spending dozens of hours researching and studying a given startup to prepare their diligence material.

60.   It’s tempting to sacrifice work on the business when there’s a lot to do in it.🛠️

This week we had 24 diligence modules to produce on 6 different companies. That’s a lot of work to do, so it’s very tempting to block off the calendar and spend zero time managing the business or pursuing important relationships in order to make sure we deliver with quality. This is a tension I personally deal with constantly as we continue to grow.

11/1/23

61.   In-person team meetings are worth the extra effort.🍽

This week our leadership team met over dinner to work through several key issues. We normally meet virtually since all of us are in different cities, but the impact of being in person together for this one was palpable. It was so much easier to connect on a personal level and our creativity levels were noticeably higher than usual. Well worth the extra effort and cost.

62.   Unreasonable valuation = dead deal.☠️

A mistake I’ve seen founders make again and again is setting the company’s valuation way too high from the start. Valuation is one of the first things that investors look at, and if it’s outside of a “reasonable” range, interest dies before they even get a chance to look at the company. I think founders tend to make this mistake either out of ignorance or out of a desire to set a strong negotiation anchor, but it backfires every time I’ve seen it happen. I realize valuation is a tricky, nebulous thing, but the key (as with any “pricing” negotiation) is to identify that “reasonable” range and resist the temptation to overprice.

63.   Competitive hack: focus on a specific region📍

This week I attended the Houston Startup Ecosystem Summit hosted by Dell for Startups at The Cannon. While there, I met a few companies claiming to be “the only X company focused on doing Y for Houston.” I found myself believing them easily. This is a perfect example of creating a local blue ocean inside a sea of red. Even if the service is similar to what is offered in other communities, localizing a product or service is immediately differentiated and defensible in the eyes of the market.

11/8/23

64.   Thoughtful analysis is difficult to produce.🧠

After almost a year of producing diligence material on a regular basis, I continue to be amazed at how much time and energy it takes to develop high-quality, thoughtful analysis. Distilling down what a startup is really trying to do, sorting through the overabundance of online data, identifying trusted sources and references, and then condensing and presenting the most important takeaways for an investor to consider always takes at least 30% longer than expected. In particular, I have developed a tremendous appreciation for solid, well-thought-out, and cleanly presented market analysis (especially since there is so much BAD analysis out there). Here’s a fantastic recent example focused on the Regional Air Mobility market from McKinsey I read this week while researching the market for an electric motor startup.

65.   Effectively visualizing a process creates the foundation for change.🧱

After a month of observing a new client’s process, this week I took the next step and mapped what I saw into a detailed workflow using the Angel Ops Framework. We then reviewed it together, made adjustments where needed, and walked away with a mutually agreed-upon baseline for the current status. This exercise created the clarity we needed to move towards delivering effective recommendations for improvement (which I’ll be presenting in a few weeks). After all, how can we recommend a change without first fully understanding the current situation?

66.   Basic training is a basic need.🏋️

This week we led a training for a client’s incoming team of student venture associates titled “Introduction to Early Stage Investing and Alternative Investments.” I was very pleased with how it went - they asked so many great questions that we only got through about half the content prepared, so we’ll meet again in a couple of weeks to finish things out. In contrast, earlier in the week I spoke to a new associate at another angel group who told me “I wish we had more training available; it’s really tough to get up to speed without it.” Something tells me I’ll be running this training again very soon.

11/15/23

67.   What does it mean to be human?👶

This week I attended a fantastic conference in DC hosted by Manas Venture Studio, and one of the topics discussed was the impact of AI. Historically, common answers to the question “What does it mean to be human?” may have included things like “creativity,” or “the ability to use complex language to read, write, and communicate.” With the rapid rise and technical capabilities of AI, these responses are no longer uniquely human, and over the next few years we will all be forced to answer this question. What do you think?

68.   Sometimes, recognizing wasted time is the best way to save time.🧗

Earlier this week, I spent about 4 hours working through an important strategic decision. I didn’t make much progress, and by the end of the day, I found myself very frustrated by what felt like “wasted” time. So I went rock climbing at our local bouldering gym to clear my head. You know what I realized? Sometimes during a climb, I discover the route I’ve chosen (which at first seemed best) is not ideal. In that situation, I can either keep trying to force it and wasting a ton of energy, or I can drop back to the previous hold and try a different path, which usually gets me to the top faster. That 4 hours may not have yielded the result I wanted, but it made me realize I needed to find a different path, which is exactly what I did.

69.   Focus creates freedom.🎯

This week I experienced how focusing on a specific product, service, or offer at the exclusion of others actually creates freedom. For much of the week, I found myself overwhelmed by the prospect of serving all the needs and opportunities that have come across our desk. It’s exhausting to consider. However, once I worked through the logic and processed it with our team, I decided to focus my energy on ensuring that we do one thing well. Since that decision point, I’ve found myself feeling more creative, free to rest, and engaged in our work.

11/22/23

70.   Ridiculous prep drives ridiculous quality.👌

This week I helped run a pitch event for a new client. Their team runs a very tight ship, and we spent weeks poring over the agenda. The final printout was extremely detailed, including minute-by-minute instructions for the entire event. Quite frankly, at first, I was intimidated by the prospect of screwing things up and getting everything off track. But you know what? It went perfectly. Sure, we had to deal with some inevitable hiccups and slight adjustments. But our intense preparation and attention to detail led to the execution of one of the cleanest, most effective, and thoughtful pitch events I’ve ever been part of.

71.   Business hack: make friends.🤝

I’ve always been fascinated with other people’s stories. So I generally try to go out of my way to get to know the people around me. This week I find myself particularly grateful for the practical value of that quality. It almost feels like I’m cheating, but these friendships have helped solve real problems in our work. Just this week, existing friendships have opened the door to new clients, new staff members, new ideas, new expertise, and more. Wild.

72.   Reputation is a powerful form of value.🏆

This week I’ve been struck by the value of a strong reputation. It’s difficult to quantify its literal value, but I’ve seen the evidence clearly on display. For example, one leader in my sphere specifically came up during the course of a half dozen conversations. Every single one of them involved both me AND the other person emphatically stating how much we respect and admire this individual. They’ll never know those conversations happened, yet they all served to reinforce the positive perception of the individual. The opportunity to work with/for/around someone like that plays a clear role in decision-making. Lesson learned: reputation matters.

11/29/23

73.   Enthusiasm matters.🌟

This week I reviewed 200 applications for a part-time bookkeeper position we’re looking to fill. The site I am using includes a clever “points” feature, where each applicant receives a limited number of points they can allocate to jobs they apply for. The basic interpretation is that more points spent = more interest and enthusiasm for the position. With hundreds of applications on the table and limited time to review, I found myself only considering applicants above a certain threshold. I think the principle applies more broadly than just interviews, but it was interesting to see myself gravitate towards those with stronger interest.

74.   Taking time off is humbling.🦃

This week, I took a few days (mostly) off to celebrate Thanksgiving with my family. It was wonderful and terrible at the same time. I love my job (most days), and one of the best, yet most frustrating, parts about it is that there are always more projects to work on than there is time in the day. Making the conscious decision to not work on those projects is, at least for me, really tough. Plus, taking a break creates a real backlog for the days after I return. By truly resting and engaging with my loved ones, I’ve found myself feeling deeply humbled. It reminds me of the reality that I’m limited, can’t do everything, and that it’s a very good thing the world doesn’t rely on me to function.

75.   Learning to fall well is an essential life skill.🧗

This weekend I got to go outdoor bouldering with some friends for the first time. Here’s a video of my first “real” outdoor fall. Here’s another video from, like, my 12th. I learned a lot from that experience, but one thing in particular that stuck out was the importance of learning to fall well. When climbing outdoors, one of the most important pieces of equipment is the crash pad - if you miss it, it’s going to hurt. So when you fall (not if, when), you better not miss it. And you better have great teammates spotting you just in case. I think this is applicable to a lot of life but to entrepreneurship in particular.

12/6/24

76.   Make time to read a lot.📖

This week I was able to have breakfast with a mentor of mine who leads a publicly traded company. He shared how over the Thanksgiving holiday, he got sick and took advantage of being stuck in bed by reading 3 books (all of which were pretty dense). That struck and challenged me because I often find myself so focused on our business that I fail to make enough time to pursue my own continuing education. I’m working on a reading list for next year - any recommendations?

77.   Process tweaks fail to address fundamental issues.🚧

Improving processes and addressing fundamental issues require very different execution plans. This week I presented a set of process recommendations to a client and realized during the discussion that some of these recommendations were incomplete. They failed to adequately consider some of the deeper underlying problems in play. While I deeply believe that instituting solid processes and operational structures can drive meaningful change in any organization, this experience highlighted the importance of recognizing when an issue goes beyond process.

78.   Startup investing is sexy.🔥

It’s easy to forget how unique and attractive this ecosystem is. This week I kicked off a set of interviews with a volunteer team of analysts serving one of our angel network clients. After speaking with just a few of them, I’m reminded of how sexy the startup investing scene is. The opportunity to be a part of evaluating a diverse range of startups and helping investors make big bets has massive appeal, especially for those looking to break into venture.

12/13/24

79.   Lesson 1: Relationships are Everything🤝

a.      Events are a great investment. (July 5, Lesson 2)

b.      Relationships are everything. (Aug 23, Lesson 1)

c.      5 killer mistakes for young founders like me. (Aug 23, Lesson 3)

d.      Referrals are insane. (Sep 27, Lesson 2)

e.      In-person team meetings are worth the extra effort. (Nov 1, Lesson 1)

f.        Business hack: make friends. (Nov 22, Lesson 2)

80.   Lesson 2: Overindex on Clear Communication📢

a.      Talking to customers about your thing is a really good idea. (Jul 5, Lesson 3)

b.      Communicating the essence of a business in 60s or less is hard. (Jul 26, Lesson 3)

c.      Terminology Matters. (Aug 2, Lesson 1)

d.      Getting people on the phone tends to reveal the real story. (Aug 30, Lesson 2)

e.      Clear communication is hard to learn, but essential to master. (Sep 13, Lesson 1)

f.        When the team is aligned decisions get made fast. (Oct 11, Lesson 1)

g.      Effectively visualizing a process creates the foundation for change. (Nov 8, Lesson 2)

81.   Lesson 3: Time is Precious.⏳

a.      Time is precious. (Jun 21, Lesson 3)

b.      Numbering your days is humbling. (Jul 12, Lesson 2)

c.      Life can change pretty fast. (Jul 26, Lesson 1)

d.      It's tempting to sacrifice work on the business when there's a lot to do in it. (Oct 25, Lesson 3)

e.      Sometimes, recognizing wasted time is the best way to save time. (Nov 15, Lesson 2)

f.        Taking time off is humbling. (Nov 29, Lesson 2)

82.   Lesson 4: Hard Work is a Required Input🔨

a.      There's only one way to earn your stripes. (Aug 23, Lesson 2)

b.      Defining a clear strategy is hard, and takes more work than you'd think. (Sep 6, Lesson 3)

c.      There’s a big difference between research and analysis. (Sep 20, Lesson 3)

d.      Thoughtful analysis is difficult to produce. (Nov 8, Lesson 1)

e.      Ridiculous prep drives ridiculous quality. (Nov 22, Lesson 1)

1/3/24

83.   LinkedIn page follower count hack: post a job.🚀

This week I unintentionally boosted our company’s LinkedIn follower count by 144%. How? I posted a sponsored job on the platform for 24 hours. We went from 262 to 640 followers overnight. Insane.

84.   Sell a product, not a service.🏭

Over the break, I read Built to Sell: Creating a Business That Can Thrive Without You by John Warrilow. It took me about 2 hours to read and was well worth the time. I highly recommend it. Main takeaway? Treat your service business like a product business and focus on building repeatable systems to deliver that product.

85.   Experience makes a big difference.🧠

Last week the PitchFact leadership team met for our annual meeting. It was truly spectacular to see how much more efficient and effective we were with our time together after a year of running the company. I’d venture as far as to say that 9-hour session was more productive than any 2 of our previous quarterly meetings combined.

1/10/24

86.   New hypothesis: HR professionals make great VCs.🦲

Over the last 2 weeks, I reviewed more than 600 applications and conducted at least 24 interviews across a few different roles. I learned a lot from condensing that much recruitment into such a short period, but one of the things that struck me was how similar the whole process feels to Venture Capital. There are a limited amount of resources to distribute (HR: roles, VC: capital). There is limited time to make a decision (HR: business need, VC: limited period for deploying capital). The best opportunities aren’t available for long (HR: candidates get hired, VC: rounds get filled). Decisions must be made with limited information (HR: application, interviews, reference and background check, VC: application, interviews, reference and background check). So my latest hypothesis is that a recruiting pro would probably make a great GP.

87.   Working with people who are better than you at a thing is insanely freeing.🆓

This week, two of our new team members got up to speed on their respective work areas, and it was so freeing to spend my time teaching instead of doing. And, since they’re both solid A players, the “teaching” process was very limited - they’re both far more skilled at their work areas than I’ll ever hope to be, so I’m pumped about what this will allow us to achieve in the years ahead.

88.   What’s the Most Important Thing (MIT)? 🎯

Every year, I pick a word. My word for 2024 is “Focus,” which is weird because I’m generally terrible at this. One of the things I’ve come to understand about myself is that I’m curious, and enjoy variety, change, and exploring new things. While that lends itself to some major strengths and benefits as a business leader, it also involves some real weaknesses and challenges. I’m learning the value of focusing each day, week, month, and year on the few most important things and letting the things that are less important fall by the wayside. That said, I know I can’t do this alone, so I’m trusting several close friends, advisors, and teammates to keep me accountable.

1/17/24

89.   Humble honesty gets the loudest cheer.👏

This week I was honored to serve for the 3rd time as a panelist for the Entrepreneurship Bootcamp for Veterans 60-second pitch, where I heard two dozen veterans pitch their business. This year, one leader’s presentation stood out: Ryan Pappas. After a week of learning business concepts and analyzing his business, Ryan realized that his existing plan was unsustainable and he needed to pivot. So, instead of making something up or presenting a vision he didn’t believe in, he stood before 30 people and told it like it was. And you know what? His honesty was met with a standing ovation and the loudest cheers of the night.

90.   Someone has to lead.👑

Leadership is vulnerable. It involves sticking your neck out, taking the heat for mistakes or dissatisfaction, and prioritizing the needs of those under one’s care. I’ve seen thoughtful leadership on display through a half dozen leaders around me this week - I’m both honored and inspired.

91.   Hiring long » Hiring wrong.🕰️

This week I listened to the Founder’s podcast episode about Charlie Munger, which I highly recommend. At the end (last 20m), David Senra shared a compendium of takeaways from a variety of entrepreneurs about hiring “A-players”, and how important this is to the long-term health of a startup. We’ve recently begun expanding the PitchFact team, and are still working through filling a couple of roles. I’ve found myself feeling a bit frustrated/disappointed by the strictness (and resultant “slowness”) of my own process, but this short highlight reel from some of history’s greatest entrepreneurs was incredibly validating that hiring long is FAR better than hiring wrong.

1/24/24

92.   Founders must learn to clearly communicate a problem.🎤

This week I had the opportunity to serve as the guest lecturer for an Engineering Entrepreneurship course at Texas A&M. During the class, we watched 4 demo day pitches, and the students were responsible for evaluating the strength of each founder’s problem. One thing that became abundantly clear during the discussion was that some entrepreneurs forced the audience to infer the problem, while others spent precious pitch time to clearly explain and define it for us. That prioritization of time made a huge difference in the class’s ability to connect with the need for each solution.

93.   Taking a vacation is hard work + great teammates are a true gift.🛫

By the time you read this, I’ll be on a plane. As most of us know, it’s always a lot of work to organize, get ahead (sort of), and prepare systems/processes to continue functioning in one’s absence. This will be my first “real” vacation since starting PitchFact, and I’ve been struck by 2 things:
1. It’s much harder to take time off as a founder than it was as an employee.
2. I wouldn’t be able to do it without a great team willing to step up and help.

Perhaps these takeaways are fairly obvious, but I’ve found myself particularly aware of them both this week.

94.   Don’t skip the reference checks.🔍

It’s tempting to skip reference checks, especially when a candidate seems like a perfect fit after multiple interviews. This week, I discovered why that step is so important. We were fortunate to have two very strong candidates, but one’s references stood in stark contrast to another’s. That distinction gave us absolute confidence in our final decision.

1/31/24

95.   Effective managers generate results and retain their people.📈

Keaton and I are currently reading “The Effective Manager” by Mark Horstman. I should’ve read it years ago. Having a clear definition of what “good” looks like in management is both refreshing and relieving. I’m looking forward to implementing what I’ve learned very soon.

96.   Solving one problem always creates another problem.✈️

This week, I reflected on the marvels of air travel. I realized the airplane is a fantastic solution to the problem of transporting humans quickly from point A to point B (when B is a long way from A). However, I also realized that new supporting problems like “keeping travelers comfortable” or “organizing flight logistics” quickly arise. By inductive reasoning, my current theory is that “markets” are basically just layered collections of connected problems and solutions.

97.   Google Translate is the greatest thing ever. 🗨️

When no one speaks English and you prefer to not roll the dice on dinner (again), Google Translate is the real hero.

2/7/24

98.   Not being in charge is deeply restful.🧘‍♂️

My wife planned our entire vacation (which she loves doing). She handled the details for every hotel, train, bus, flight, and more. Besides being incredibly grateful for my bride’s skillset, I found that the simple reality of having someone else be “in charge” was incredibly restful for me. I was able to just “go with the flow” and enjoy. So much of my day-to-day is characterized by decision-making that it was wonderful to not be required to do so for a few days.

99.   Just because a company is doing well does not mean it’s ready for investment.💰

This week we evaluated a strong, compelling company with meaningful traction and exciting growth prospects. Very investable. But they weren’t ready to pitch - they had not yet finalized the mechanics of their raise, the “pitch” needed some work, and the company structure was unclear. With a little work, they’ll be in a great position, but my takeaway is that being investment-ready goes beyond simply having a strong, growing, investable company.

100. Values resonate differently with each team member.🌟

At this month’s staff meeting, we reviewed PitchFact’s 5 core values: eager execution, highest standard, transparent together, rest well, and lean in. I consider them all equally important, but realized that they resonate differently with each person. For example, one team member mentioned that “lean in” is super important to them, another highlighted “eager execution,” and two mentioned that “rest well” stood out to them.

2/14/24

101. Trust is more valuable than money.🤝>💰

I continue to be reminded of the invaluability of trust. A half dozen introductions, meetings, and new projects arose this week that never would have happened in the absence of trust.

102. Getting trusted clients in a room together is a good idea.📆

This week two of our most dedicated clients were kind enough to join me for a 1-hour video call. Instead of “tinkering in the dark” we decided it was a better use of time to propose a product idea to them and see what they thought. The call was extremely helpful. I left with a much clearer picture of what is important to each client and a clear path forward for how to proceed. Well worth the effort to coordinate.

103. Having a team is the greatest thing ever.👥

I’m continuing to learn how to delegate. It’s fantastic. This allows me to focus my time and energy on projects and activities that are of the highest value to the company and that I’m best suited to. It’s a work in progress, and it’s not been easy, but I’m excited to continue growing and investing in our team.

2/21/24

104. Defining clear “axes of better” is the starting point for strong positioning.📈

In a very helpful conversation this week focused on improving PitchFact’s positioning, I was encouraged to consider the 2 “axes of better” that make PitchFact stand out from the primary alternatives. This would form the foundation for our simple positioning statement, and also allow us to build a pretty graph where our logo shines in the top right corner. Fun project.

105. Investors dislike feeling rushed.💨

I’ve noticed founders often play the scarcity card (whether intentionally or not) by mentioning their round is almost closed or by proposing a firm close date. More often than not, the angels we work with tend to be off put by this, and will instead opt to pass on the opportunity since there’s “no time” to run through their normal process.

106. Complementary partnerships alleviate the pain of saying “no”.🤝

We can’t do everything. At first, it was easy to say “yes” to anything that was interesting while we got the company off the ground; now we’re learning to say “no” to things outside our core competency and (try) to stay focused on what we do best. That’s where I’m finding partnerships with complementary service providers to be very helpful. For example - need pitch coaching? I’ve now got a great referral list for that. Want help marketing your community, need someone to run an event, or want support for ongoing post-investment updates? I’m working on partners for all those.

2/28/24

107. I need wise counselors to help me focus and not overcomplicate stuff.🔍

I’ve probably written about this lesson learned a half dozen times over the last year, but I’m continually grateful for wise outside voices speaking into our business. I tend to overcomplicate things and get stuck in the weeds. I waste a lot of time doing this. To anyone who’s ever told me I’m doing something dumb and helped me focus on what’s actually important - thank you.

108. Compliments and feedback are so meaningful.📢

This week our team crushed a set of 4 diligence reports, and we received no fewer than a dozen compliments from investors about how helpful they were. Let me tell you, positive feedback is just the best, especially when there’s a team to pass that feedback along to. It helps make the hard work all worth it.

109. Hiring a good offshore admin/VA is harder than I thought.👂

Of the several roles we filled over the last few months, I expected this one to be the easiest. Contrary to that expectation, I’ve struggled here more than anywhere else. If anyone’s got wisdom to share on hiring part-time offshore VAs, send it my way - I’m all ears!

3/6/24

110. Marketing is hard.📣😓

I’ve been working on updating our brand positioning and preparing for a few upcoming conferences this week. It’s a lot of work. I’ve realized that I have a ton to learn about how our product is perceived by the market. On that note, I could use your help: what’s important to YOU when it comes to due diligence? Fill out this 1 question survey and as a thank you I’ll send you the Angel Ops e-book I’m working on as soon as it goes live.

111. Bad sales is a bad time.🙅‍♂️

This week I got angry. I had a problem, spent time online to find a company I thought could solve it for me, scheduled an intake call with the sales team, and spent the first 7 minutes of our call explaining to the sales guy the full background and exactly what I was looking for. Pretty big investment on my part. He then proceeded to completely ignore everything I had just said and walk through what was obviously a cookie-cutter sales script, most of which was completely unnecessary. All I wanted was for him to say “Yep, we can definitely help. Here’s how to get started.” But I felt so unheard, and the conversation felt so gross that I decided there was no way I could work with this company.

112. “Unique, One-of-a-Kind Experience” is an incredible value proposition.🥃

This week Dani took me to Oak and Eden in Bridgeport, TX for my birthday. Their “secret sauce” is an in-bottle finishing technique where instead of finishing the whiskey in a second barrel (the usual “double barrel” approach) they finish by dropping a 5” wood spire into the bottle and leaving it for a couple of months. What’s cool about it is that they’ve come up with dozens and dozens of spire variations or “flavors”, and allow guests to essentially build their own whiskey by choosing the base and spire they like best. I think it’s genius and a great example of how to stand out from the crowd. In case you were wondering, after tasting a few variations, I went with the 116-proof bourbon base and a French oak spire with a cherry liqueur infusion. Ask me how it turns out in 2 months.

3/13/24

113. “Changing the blade” is a great investment.🚜🌱

This week I gave my lawnmower some TLC. I replaced the blade, greased the wheels, changed the air filter, and generally cleaned it up. I couldn’t believe how much of a difference it made. Mowing was easier/faster (felt like 20% ish faster) and the grass looks noticeably better. Takeaway? Spending resources to keep your tools sharp and running smoothly is a great investment. This applies to business skills, teams, and organizations just as much as it does to my yard.

114. Consistency pays off.📖

As you may recall, last year I wrote about a different segment of Angel Ops nearly every week for about 6 months. This weekend, I repurposed much of that content to finalize the first draft manuscript for the Angel Ops e-book, which we’ll be releasing in the coming weeks. It was deeply rewarding to see the thought and time I poured into those weekly articles compiled into a single, high-quality resource with over 25,000 words. Want to be notified as soon as it goes live? Complete this 1 question survey.

115. Focus on the problem.😵

A few weeks ago I wrote about the importance of understanding the problem. This week, I was punched in the face by my failure to follow my own advice - I overengineered a solution that I never even got a chance to present because, upon further discussion with real live customers, it became evident that I was solving the wrong problem. Oof.

3/20/24

116. The stuff that moves the company forward is usually the hardest to find time for - there’s no deadline other than what you provide for yourself.⏳

Saying “no” to urgent demands is tough. But I’ve realized prioritizing the important over the urgent is incredibly valuable. These important but not urgent projects tend to have the highest value for the organization because they drive growth and progress. Lesson learned: figure out how to focus, say no, manage expectations, delegate - whatever you have to do to get the important stuff done too.

117. DO NOT push website changes unless you know what you’re doing.🚨

This week I killed our website for half a day. I was trying to spin up a new landing page and totally screwed up the site’s settings, which then took me half a day to fix. On the bright side, now I know how to throw together a decent landing page in just a couple of hours AND fix DNS settings.

118. Cold email does actually work (sometimes).🎯

I can’t believe it but this week I responded to a cold email. I couldn’t help it. I probably get 2 dozen of these every week, and almost all of them are auto-deleted or unsubscribed. But this one was tailored to exactly a problem I’ve been trying (unsuccessfully) to solve and the language wasn’t trying to be overly cute or clever.

3/27/24

119. Sometimes getting your hands dirty shows you what to clean first.🧤

This week our lead designer was out of the office, so I was responsible for the design work on 3 reports. I learned a TON about how things have changed in the last few months since we began to grow our team, and realized through the experience that there was some work to do to improve our process. I would never have realized this if I hadn’t been forced to step into the role.

120. You can’t get back up unless you get knocked down.🥊

This week I got punched in the face (figuratively). It was rough. I learned about a new, well-funded semi-competitor that I wasn’t previously aware of, and at first I was pretty bummed. So I let myself be sad for a day. But when Monday rolled around, I got back up, hit the ground running, and am as confident as ever that we’re onto something big here at PitchFact.

121. Don’t overthink it. Way more enjoyable.🪵

I definitely overthink it. A lot. But this weekend, a friend and I built a small wooden side table together as a way to catch up, and I am proud to say I went in with no design or plans, just my own (very mediocre) DIY skills and a trip to Lowe’s. The product was a solid 6/10, but let me tell you I enjoyed the experience 100x more than I would’ve if we tried to overengineer the thing together and ended up getting nothing built.

4/3/24

122. ALWAYS order samples.📄

This week I spent some money to order samples of the flyers I’ve been working on for an upcoming conference. Boy am I glad I did - they were close, but having them printed and on my desk made it VERY easy to identify small details that were off that I would have otherwise missed.

123. Cash flow forecasting = well worth the effort.📊

This week we worked on a detailed cash flow forecast for the business. This effort has been extremely liberating because it has revealed where we do and where we do not have room in the budget for the variety of projects and opportunities we’ve been considering. As our bootstrapped business has begun to grow, I’ve found myself struggling to clearly understand what we can afford and when, so this effort has been fantastic.

124. Be different.👨‍💻

At a networking event this week I met a very nice entrepreneur who runs a web development agency. I will never refer anyone to him ever. Before I tell you why, let me summarize the gist of our conversation:
Me: “What kind of projects do you specialize in?”
Him: “Oh, we do everything.”
Me: “Ok, who is your target customer?”
Him: “Oh, we’ll work with anyone.”
Me: “Ok, what price range do you typically charge for the average job?”
Him: “Oh, it depends on the project.”
Me: “…”
I walked away from this conversation deeply bothered by how undifferentiated this company was. In an effort to please everyone, he’s built a business that likely pleases no one. I have no idea what he’s good at or when I should send someone his way. Lesson learned: be different.

4/10/24

125. Deadlines are a gift - they help draw a line in the sand at “good enough”.⏰

I’m working on several creative projects right now - an e-book, some flyers, banners, multiple landing pages, etc. I could iterate endlessly on all of them if it weren’t for the reality that I’ve got due dates on every single one. One of my professors used to say “Don’t let perfect be the enemy of good,” and deadlines are very helpful in that effort.

126. Make your objectives and key results clear to everyone in the organization.🪨

I’ve been reading “Measure What Matters: OKRs: The Simple Idea that Drives 10x Growth” by John Doerr. It’s fantastic. But one of the simplest ideas that struck me this week was the need to publicize each person’s focus - from top to bottom. We’ve leveraged the EOS idea of “rocks” from the very beginning, but this is a nuance we’ll be implementing very soon.

127. Be prepared - always.☕

This week Dani and I (and our 2 dogs) drove through Austin on the way to visit family for the weekend. We stopped for coffee at the best coffee shop in the world - Merit Coffee - to get a bit of work done and enjoy the weather. Somewhere between the Subaru and the patio table I looked up and found myself laughing at the smallness of the world. A friend I’ve done some work with and who I had just met with virtually the day before was having coffee with someone who was new to me. But as it turns out, that person works closely with another connection I have been meeting with over the last few months about a separate project. Kinda crazy, but lesson learned - always be prepared, you never know who you might run into.

4/17/24

128. Having a team you can trust is the actual best.👥

I continue to be more and more grateful for the PitchFact team. Seeing our reports come together without my involvement has been a fantastic blessing that has allowed me to focus my time on growing and managing the business. This week in particular I found myself feeling very grateful. We delivered 4 diligence reports, but instead of spending hours researching the intricacies of the kids baseball video recording industry, I got to spend the week on business development and networking with like-minded investors and entrepreneurs at the Lions Den DFW.

129. Know your assets.🔍

While in Dallas I got to be part of a whiteboarding session with several trusted peers in the impact investing and wealthtech world. As part of that conversation, we focused on understanding our collective “assets” and the key “opportunities” we see. I hadn’t previously been forced to verbalize what PitchFact’s core assets are, and it was pretty cool to find myself describing the real and unique value we bring to the table.

130. Discovery never stops.🌟

This week I got to grab drinks with an angel investor who’s been using our product for over a year to hear his thoughts and understand how our work fits into his investment process. He had some fantastic insights for me, and I am very excited to “get back on the field” this quarter to continue our discovery efforts.

4/24/24

131. Clean financials are music to a banker’s ears.🎶

I met with 3 bankers this week. I was surprised to hear every single one of them comment on how well-organized and clean our financials were. I guess paying for a good bookkeeper is less common I thought.

132. Say no.🚫

This week I said no to a half dozen opportunities I was pretty excited about. That allowed me to prioritize what’s most important. It didn’t feel great, but it felt right, and it’s a pattern I aim to continue.

133. How to lose a customer 101: blame the customer and make them fight you.📉

This week I realized some businesses don’t understand the concept of LTV, and some do. Amazon’s return, shipping, and customer service policies are incredibly easy and simple. They definitely lose money on quite a few individual transactions as a result of this ease. In contrast, Dani and I recently sold something through another marketplace (ask me separately if you want to hear the full rant) and I got slapped with a massive unexpected shipping fee. After fighting with customer service for over a week, we got nowhere and are pretty much stuck with this insane fee. Maybe the marketplace protected their bottom line on this deal, but we’ll never do business through their platform again (where we otherwise would have). Was it the right business decision on their part? Absolutely not. Next time I’ll stick with Amazon.

5/1/24

134. Don’t let perfect be the enemy of good - just make a decision.✂️
This week I spent way too much time agonizing over the minute details of a simple flyer we’re handing out at an upcoming event (come see us at the Angel Capital Association Summit on May 13-15!). I finally cut myself off from any more tweaks and let good enough be good enough.

135. Angel investors each have a unique approach.👼

I met with two different angels over the last 2 weeks to gather feedback on our work and how they approach angel investing. Both were very different. This quarter I’m aiming to interview 10-20 angels about their approach - interested in discovering what patterns emerge. Want to be included? Shoot me a note.

136. Ask for help.🙋‍♂️

We’ve been trying to hire an admin/VA for a few months now. After failing to find a good fit multiple times, I asked for help from a friend. They were kind enough to share 6 pages of notes and a walkthrough of exactly what they did. Thanks to that coaching, I’ve made several adjustments to our approach and am much more optimistic going into the next attempt. Fingers crossed!

5/15/24

137. Member engagement is tough for everyone. 💬

Apparently, the typical angel group sees anywhere from 20-30% member churn every year. Anything below 15% is fantastic. Lots of strategies for improving member engagement, but defining what type of engagement is important to your group is the first step to improving it.

138. 30-40% of Angel Networks operate with some kind of fund attached. 🔗

This was surprising to me. It’s growing more and more common for angel groups to offer and/or require participation in some form of an associated fund. I was impressed by the variety of fund structures at play, and this is something I am curious to explore in the coming months.

139. We need more case studies.📖

Angel groups generally understand how “diligence as a service” could benefit them. But why should they trust us, some company they don’t know, with something as important as due diligence? It’s a fair question, and I was encouraged to build out a few solid case studies highlighting the value we’ve delivered. We’ll bring some next year!

140. Bonus: Andes mints are God’s candy. 🍫

We went through 2 boxes in 2 days, and everyone snagged some. Next time we’ll get smart and tape the mints to our flyers!

5/22/24

141. Sometimes the best business meetings involve no “business.”👥
This week I had a meeting on my calendar with another founder to discuss a possible partnership. We spent the entire meeting talking about family, faith, culture, and our top book recommendations. Yet I left feeling even more excited at the prospect of working together. As one of my mentors always says - relationships are everything.

142. Seeing your team grow and mature is so satisfying.🌱

Keaton and I tend to follow the “Model, Assist, Watch, Leave” training framework. I’ve been modeling how to lead a particular meeting for one of our team members for several weeks, and this week we transitioned to the “assist” phase. Watching them step up and do well was deeply fulfilling in a way I didn’t expect.

143. Communicate, communicate, communicate.💬

This week I made a classic sales mistake. In my enthusiasm about a new opportunity, I committed us to something without first validating we had the capacity to fulfill it. We’ll figure it out (startup 101), but a lesson learned: communicate and confirm availability before committing the company to something.

5/29/24

144. SOPs = Leverage🔧
This week I spent a lot of time drafting and editing Standard Operating Procedures (SOPs) for several internal processes. It’s exhausting, but WOW I’ve been amazed by how quickly the leverage shows up. Now others can handle things I previously was responsible for easily, repeatably, and with quality. Life changing.

145. Growth is pain.🌱

I recently heard a quote that stuck with me this week. “If you want to grow, expect to suffer.” It’s easy to coast, to enjoy the status quo. Changing, growing, improving, or developing something takes effort, sacrifice, and some measure of pain.

146. Warm leads are truly a gift. 🎁

The kindest thing you can do for a growing company is think of them when you have a problem they might be able to solve. This week I was blessed to receive a few warm introductions, and it was fantastic.

6/5/24

147. The hardest part about market research: not getting distracted.🔍
This week, I stepped in to help draft one of our 5-page diligence reports. The company I analyzed is developing a new high-performance material for use in 3D printing. So I spent the weekend taking a deep dive, looking at competitors, market size data, and more. The hardest part? Not getting distracted and endlessly researching all the cool similar/related technology.

148. The diligence lead naturally develops a deeper level of understanding.🧠

We realized this week that the depth of understanding available to an analyst or investor who leads a diligence call is a step beyond an analyst/investor who watches a diligence call. The preparation and increased engagement demanded by asking thoughtful questions make a noticeable difference in retention. For example, one of our team members identified several potential competitors after reading the company’s deck and watching the diligence call. And they were great. But after spending several hours with the founder myself and doing my own market analysis, I realized that there were better, more direct competitors worth mentioning instead.

149. Founders can be a great source of warm leads.🤝

We’ve recently come to understand that even though entrepreneurs are not our customers (we exclusively and intentionally offer only buy-side diligence), there is a way we can help. By offering to hop on a phone call with any prospective investor interested in taking a look at the diligence materials we have produced on their company, we’re able to enhance their credibility, help their prospective investor make a better decision, and engage with a warm lead in one 30 minute phone call. Huge win-win-win.

6/12/24

150. “Buy to try” is often the cheapest research for busy decision-makers.🛒
I’ve become cognizant of a reoccurring pattern in recent weeks. It seems like, when faced with a problem, busy leaders (myself included) would prefer to do the bare minimum amount of research/vetting and commit to a “trial” purchase instead of deeply analyzing a solution beforehand. We’re working on leveraging this insight to make it easier/cleaner/less friction-filled to try our product in a new use case.

151. Don’t count your chickens before they hatch.🐔🥚

The simple truth I was reminded of this week: a deal isn’t done until it’s done.

152. 75% selling, 25% scaling.💼

A mentor encouraged me this week that the most important use of my time is 75% selling, 25% scaling. I like to get distracted by shiny things, so this reorientation was a helpful lesson.

6/19/24

153. Picking up the phone is sales magic.📞
Email is a great tool. But let me tell you, it’s CROWDED. People still pick up their phones, and a few intentional phone calls this week have proven exceptionally valuable.

154. Make time to think.🧠

This week I spent some time intentionally reflecting on the state of our business. It’s been several weeks since I’ve been able to carve out space to do this, and I’ve been reminded how important this is as CEO - if I’m not doing it, who will?

155. Just show up.📅

Due to a variety of factors, I found myself feeling pretty discouraged several days this week. But the saying “just show up” stuck with me, and I’ve been reminded of the importance of consistency no matter the circumstances.

6/26/24

156. Time is precious.⏳
Owning a business has taught me a lot about time management, but being a father has taken that to another level. She’ll never be this age again, so I want to take every opportunity I can to be present. How I choose to spend my time right now, every day shapes the kind of father I will ultimately be. In the same way, you and I will never be this age again - we only have one life, lived 24 hours at a time. I’ve found myself hyper-focused on creating leverage, and gladly exchanging resources for time where I once might have “done it myself”. This focus requires me to say “no” to things that are not a “heck yes”.

157. Ordinary is beautiful.🌸

Never before in my life have I been as excited to see someone smile as I was the first time our daughter looked me in the eyes and grinned. Over and over again the last few weeks, she’s experienced her “first.” Life, and all the distinctly ordinary things that it’s composed of - taking a bath, going for a walk, smiling - is an incredible gift that I hope to never take for granted. This has brought new meaning to the daily, ordinary tasks I get to undertake as part of my work. Writing this post each week. Meeting with our team. Talking with customers. Strategizing and planning. Even sending emails and doing administrative work. It’s all part of the game, and I love it (even if it’s exhausting sometimes).

158. Help is glorious.💖

I am so, so grateful for the community of friends, family, and teammates that have supported us during this season. The prospect of doing this parenting thing alone sounds awful, and I’ve found myself developing a new level of appreciation for the people who choose to lean in. This applies professionally as well - the men and women who have sacrificed their precious time to lean into my journey are a gift, and I aspire to pass the favor along to the next generation.

7/3/24

159. Quarterlies are SO ENERGIZING.⚡
I get fired up after every quarterly meeting. This week, Keaton and I wrapped up our regularly scheduled 8-hour sit-down (in-person, too!). “An 8-hour meeting?!” You may be thinking to yourself. Yes, and that’s never long enough - we could have easily met for another 8. I don’t know how big businesses get anything done. But man I left that meeting fired up and ready to get to work. If you’re running a business and looking for a solid management structure, check out the EOS Model.

160. A newsletter has to solve a problem for the reader.🧩
This week I popped into a few sessions of Commacon, where newsletter gurus like Alex Lieberman, Tyler Denk, Polina Marinova Pompliano, Justin Welsh, and more shared their experience and expertise. One of my biggest takeaways is that for a newsletter to grow, it has to solve a problem for the reader. Historically, the Diligent Observer has not had a clear “problem” in mind. Well, now it does: Helping angels make better bets.

161. You never know what experience will end up being relevant.🔄

This week I sat down and built a rudimentary order-processing/management system for our team. Until recently, we’ve been able to get by with fairly informal systems, but as we grow this structure will help us not drop the ball (we hope). I started my career in technical sales, and I was shocked by how quickly I was able to build a functional tool because of that experience. Ya never know what will end up being useful somewhere down the road!

7/10/24

162. Feedback is only useful if contextualized.📝
We’ve produced 150+ reports over the last 18ish months, and 98% of them were between 1-5 pages in length. But two were much more in-depth: a holistic 37-page analysis of a company developing a new battery technology, and a 12-page analysis of the charity management market. Most of the feedback we received was that these long reports included “too much detail.” Contrast that to this week, when I met with a family office that prefers to lead funding rounds and go deep in their analysis. Guess what feedback they gave me? They want the 37-page analysis, and the 1-5 pagers aren’t nearly detailed enough. Context matters.

163. Show me your rocks.🪨

Our team recently set new “rocks” (from the EOS model, things that must get done during a given period) for Q3. Historically, I’ve made a point to share company-level rocks with our staff, who then set their own personal rocks for each period. But since reading Measure What Matters by legendary VC John Doerr, I’ve learned that not only should I be sharing executive-level rocks, but each individual should also make their own rocks public. This enables horizontal support and accountability. This quarter we’re giving it a try.

164. People want to share their expertise.🗣️

Over the next few weeks, I’ll launch the “Expert Perspective” series as part of The Diligent Observer. This content will be focused on helping angels make better bets by interviewing individuals with relevant expertise. I’ve already got a half-dozen interviews lined up, and so far everyone I’ve asked has been willing to participate. It seems like most people want to share their expertise with the world, even if it costs them a bit of time. I’m pretty excited about this. Know someone I should interview? Send me a note, I’d love to chat.

7/17/24

165. I gotta learn to sell the company, not just myself.🏢
This week we kicked off a new project, and the customer seemed disappointed that I wasn’t personally the one who would be performing all the analysis. While I appreciate the trust and relationships I’ve gotten to build over the last few years, I’m realizing more and more how important it is for me to learn to sell the value of the company and our team, instead of MY value. Something I’ll be working on more intentionally over the next few months.

166. Defining what problem we’re NOT solving is just as important as defining which one we ARE solving.🚫✅

Startup 101 is to know and clearly define the problem you’re solving for a customer. But I’ve recently been learning that clearly identifying what problems we are NOT solving for them may even be more important. If we try to do everything we’ll accomplish nothing, but if we do one thing extremely well, we might actually have a shot at getting it done.

167. Turn up the volume.🔊

I have been tasked with what feels like a very aggressive goal of growing our subscriber base to 500 by 10/1. We’re launching a few initiatives to help get there, and one of those is an evolution from 1-2 social posts per week to about 20 across both LinkedIn and X / Twitter. Let me tell you, managing 20 posts per week is a very different experience from managing 1! But I’ve already learned a ton and am excited about this new rhythm.

7/24/24

168. Podcasting is awesome - why did I wait this long to start?!🎙️
Whether the world appreciates these podcasts or not, I’ve had a blast kicking off the process. Getting the opportunity to sit down and learn from other smart people’s experiences - and to share that with the world - has been truly incredible. I’m only 3 interviews in, but I’m pumped to continue connecting and learning.

169. Bob the Builder is a genius.👷‍♂️

I’m currently reading “To Sell is Human” by Daniel Pink, and one of my takeaways is around the concept he calls “buoyancy.” Basically, this means being able to survive rejection & disappointment through positive self-talk. One of the methods for achieving buoyancy is during sales preparations to ask oneself “Can I move this person?” This stands in stark contrast to the typical sales guru’s advice to look in the mirror and hype yourself up. Instead, it focuses the mind on finding ways to accomplish the goal. Bob the Builder’s classic saying “Can we fix it?” is an amazing example of this approach in action.

170. Sometimes you can’t keep all the plates spinning.🍽️

Ever see the old circus trick where the performer spins a dozen plates on the end of several poles? That’s how running a startup feels. I think about my various tasks/responsibilities in 3 categories: one-of-a-kind china plates, nice (but not irreplaceable) clay plates, and indestructible plastic plates. I’d like to be able to keep them all spinning at once, but this week I dropped one. I wasn’t happy about it, but thankfully it was only a plastic plate, so I can easily pick it up and get it spinning again.

8/1/24

171. Community builders are rare and valuable.🤝
This week I realized that I deeply appreciate and respect the people around me who go out of their way to build community, especially in the professional sphere. The ability + drive to create space for like-minded people to connect is something special, and I aspire to grow in this skill over the coming years.

172. Focus focus focus.🎯

It is so easy to get distracted by the 1 million things I could be doing. It is so hard to stay focused on the 1-3 things that I must get done.

173. Critical feedback is like unwrapping a gift and discovering it’s a pack of socks: kind of disappointing, but super useful.🎁🧦

Was fortunate to receive some critical feedback on my work this week. It stung a bit, but I’m so grateful for it and am confident it will make my work better/more valuable in the coming days.

8/8/24

174. I have dramatically underleveraged the Substack ecosystem.📈
I spoke with a friend who built their substack from 0 to almost 1,000 subscribers in about 3 months. Pretty impressive. Apparently a key to that growth was really leaning into the Substack ecosystem. So I spent the weekend learning everything there is to learn about the platform. I’ll be posting notes, comments, and a whole lot more more in the coming days.

175. Angel investing is a mystery to many entrepreneurs.❓

This week I had the pleasure of speaking on a panel discussion with a group of 12 entrepreneurs at the Rice Alliance Clean Energy Accelerator in Houston. The panel was focused on helping these founders understand how to successfully engage with Angel Investors. Many of the questions were quite simple, such as “What’s the difference between an Angel and a VC?” It was a good reminder that angel investors are an enigma to many founders.

176. Roofers are hardcore.🏠

We got a new roof this week. The install crew got the job done in less than a day, and it looks great. Gotta say, was impressed by the work ethic and grit it takes to work through 100+ degree heat and get the job done so quickly.

8/15/24

177. Scaling a content strategy is addictive, and it’s stupid hard to stay focused.📱
Nowadays, all I want to do all the time - always - is check my notifications. It’s so addicting. Do people like our stuff? Are we getting engagement? What are they saying? The dopamine rush is crazy - I’m learning it’s important mandatory to NOT have these apps on my phone and to be incredibly strict with how much time I spend tracking and checking on the latest updates.

178. The hardest part of being a podcast host is shutting your mouth.🎙️🤐

After recording 6 podcast episodes, I’ve realized being a great host is not as easy as it seems. It basically boils down to making the guest feel comfortable, asking thoughtful questions, and listening with vigor. That last part is the hardest - it’s easy to come in with a list of questions and an agenda. But I’m noticing that the best, most interesting content tends to surface when I throw away my notes, pay close attention to what someone is actually saying, and pull on the threads that stick out.

179. Slow ≠ no.🐢

About 6 weeks after completing our first job for a new client, we were finally able to connect to discuss their feedback & next steps. I was disappointed with how slow things moved, but their feedback was glowing and we now have clear next steps in place. Lesson learned - slow does not mean no.

8/22/24

180. I finally realized why everyone sounds amazing on a podcast.✂️
It’s because there’s somebody with a trigger-happy delete button sitting in a dark room editing out all the “ums” and “uhs”. Having now fully produced 5 podcast episodes I’ve realized how easy it is to make a speaker sound so much better by killing those dreaded filler words.

181. A CEO’s job is to focus the organization.🎯

I’m not great at it. I get distracted and excited and want to say yes to all the great ideas that emerge. But I’m learning. Gotta keep putting that magic two-letter word to use...

182. Underappreciated life skill: the ability to distill.🧪

This week I helped a founder cut their 50-slide read-through deck down to 10-ish presentable slides. It was rough. The ability to distill a complex topic down to its essence is hands down one of the most underrated skills in business.

8/29/24

183. Leverage makes no sense to most people.🔧
I spoke to a class of engineering students this week about takeaways from my career. One of the takeaways is that time is more valuable than money, and I used the word “leverage” several times before realizing they had no idea what I was talking about. This tracks - most of us seem to think “How can I accomplish this task” instead of “Who should accomplish this task?” It wasn’t until I became an entrepreneur that this concept started to hit home.

184. Thinking time is underrated.🧠

This week I spent 7 hours alone in the car. It was wildly productive. Rarely do I have such a long time to chew on problems, plans, and decisions.

185. I’m an open book for better or worse.📖

I tend to be pretty straightforward and open. This is a personality trait I’m proud of, but it has downsides. Sometimes I overshare. Sometimes I step on people’s toes. Did both this week…

9/5/24

186. Underrated skill: notetaking.📝
I never go into a meeting without a notebook and pen. This practice does 3 things: 1) it honors the person I’m speaking with by showing them their comments are worth writing down, 2) it helps me retain what they’re saying by writing down the main points, and 3) my memory is terrible so it gives me a record that I can look back on to “cheat”. I’m finding that this, combined with keeping a detailed calendar works really well. For example, this week I looked up a meeting date from 2022 in my calendar, found that physical notebook entry (I’ve got literal STACKS of filled-out notebooks), and used those findings to shape a customer interaction. I know there are more efficient ways (way too many notetaking startups out there), but hey, this works for me.

187. Innovation hack: talk to customers.🗣️

We’ve recently developed a service to help angel communities access deals that other angel groups are investing in. I’m pretty pumped about it - big burning problem in the ecosystem today. The MVP’s scope and my ability to message it have evolved, streamlined, and improved in direct correlation with the amount of time I’ve spent in conversation with prospective buyers about it. Crazy how talking to customers does that…

188. People prefer to lurk.👀

We’re (probably) going to miss our quarterly subscriber goal for the newsletter. Bum. With our recent content strategy evolution (weekly podcast, posting 2x/week), we’ve seen all the vanity metrics go up and to the right, which is nice but not what we’re prioritizing (*cough* thanks Matt *cough*). And while sub growth has accelerated, it’s been slower than we expected. One theory I have is people prefer to “lurk” - watch/observe but not participate, so the “offer” has to be extremely compelling for them to subscribe. What do you think?

9/12/24

189. Do your own thing. It’s way more interesting.🎨
This week I was appreciating the uniqueness of several influential creators. One of them literally doesn’t have email and records these ugly videos highlighting people he meets throughout the week. Another firehoses the world with cool statistics from their database. Another shares business hot takes in a pithy format. All of them are (at least on the surface) comfortable and confident in their own style, and aren’t overly concerned about what everybody else is doing. That’s why I read their stuff.

190. Say “Yes and…”➕

I’m currently reading “Improv Wisdom” by Patricia Ryan Madson, a Stanford Drama professor. One of the core tenets of a good improviser is “accepting every offer.” What this means is always building the story by saying “yes and” instead of “no because.” While there’s certainly a place for the word “no” (especially as a time-strapped entrepreneur/dad/friend/etc), I love this mindset and am thinking about new ways to apply it.

191. Keep the main thing the main thing.🎯

Every year my wife and I pick a word for the year. Here’s my “word” for 2024: “Focus.” Was convicted this week on some drift. Course corrected.

9/19/24

192. Mechanical keyboards are like typing on butter.⌨️
I had no idea what I was missing out on. This week I upgraded to a mechanical keyboard and tested out several different options before landing on a winner. It’s like typing on butter. Here’s my new setup.

193. Communication hack: say the other person’s name.👂

Over the last couple years I’ve listed to over 1,000 startup pitches. Listening to a fantastic one today from an experienced entrepreneur in the skincare space, and this observation hit me: “He keeps saying his conversation partner’s name.”

This has 3 benefits: 1) Grabs listener’s attention. 2) Shows that the message is tailored. 3) Invites a response.

I’ve noticed great communicators do this constantly.

194. “You can’t expect to be great every day, but you can show up every day.”⏳

My wife gave this brilliant advice to a friend this week, and it’s stuck with me. Just. Keep. Showing. Up.

9/26/24

195. Different types of investors appreciate different types of deal flow.🌀
There are 3 types of deal flow any investor community sees. 1) Top of funnel: the thousands of applications that come in every year. Mostly declines. 2) Mid-funnel: the deals that pass initial screening based on the investor group’s typical criteria and “might be interesting”. 3) Bottom-of-funnel: the deals that have $$$ commitment from another trusted investor. I believe tier 3 deals are the most valuable for the typical angel community due to the “signaling”. Interestingly, this week I met with an early-stage VC who was specifically not interested in tier 3 deal flow but only wants to see tier 2 deals. Reason? He’s looking to get in early and lead bets on emerging technologies that are non-consensus.

196. Anchoring drives perception of quality.⚓️

Last week I flew to Seattle for a short vacation with the family. Boarding a plane with a 5-month-old is a bit of a challenge, and we did it 4 times. The boarding agent for the first flight was extremely welcoming and friendly - he made it super convenient for us. He even carried the gate-checked stroller to the plane on my behalf. The other 3 agents were fine, but nothing special. Since my experience with the 1st agent anchored the rest, my “quality” rating for the other 3 agents was much lower than it might have been otherwise.

197. People like to see cool startups. And startups appreciate press. 🚀📰

Last week I released “14 Texas Startups to Watch.” It got tons of engagement, from both investors and the founders who were featured. Will work on sharing more in the coming months.

10/3/24

198. The line between selling yourself well and gross self-promotion is very thin.🗣️
While trapped in a painful conversation at a recent networking event, I was struck by this thought. Someone talking about themselves and their work is fine; after all, learning about what other people are working on is part of what makes networking fun. But it’s SO SO SO IMPORTANT to balance that self-disclosure with genuine curiosity about others. Otherwise, the counterparty is 100% leaving that conversation with a bad taste in their mouth.

199. Key product mgmt question: Where do you want to spend your resources?🎯

This week I had a super helpful product conversation with Eric Schneider, an experienced entrepreneur and fractional CPO. My biggest takeaway? “You can’t do everything well. Focus and outsource/automate the rest.” Also a lesson in networking: Eric has delivered huge value for me without requiring anything in return. THAT is how you network well, and that’s why I’m happily sharing his name (unprompted) with you.

200. Consistent thoughtful content really does earn street cred.🎙️

I felt something shift this week. If you’re reading this, you may know I’ve spent a ton of time and energy building The Diligent Observer brand over the last year, and especially over the last ~3mo with the launch of the podcast. This week, I had multiple conversations where someone referenced the pod/newsletter, and something felt different about the tone. It’s like there’s a new level of respect and appreciation for what I have to say and for the PitchFact brand. Pretty cool to experience.

10/10/24

201. Organization is kindness.🗂️
The longer I’m in the business world the more convinced I become that this is the case. Remembering important details about people around you, showing up prepared and on time, being responsive, and communicating clearly - these things show honor to the counterparty (at least here in the US). This sounds simple, but consistently doing these things really does set someone apart since so many miss the mark.

202. Sometimes a 6.25/10 meeting is a 10/10 value.🤔
Over the weekend my business partner Keaton and I broke from the usual structure of our quarterly 8-hour pulse meeting. Why? We needed to hash out some key decisions around strategic focus. We spent WAY more time on it than planned, and it totally exploded our agenda. But while the meeting (which we rated a 6.25/10) was kind of gross to experience as a result, we now have strategic alignment and a clear path forward. I call that a 10/10 value for the organization.

203. Being the right person at the right time is crazy fun.🎉
One of the smartest people I’ve ever met bought me lunch this week. And it was so much fun. She’s literally 1 of 3 people in the world who specializes in her research area, and yet she was coming to me for advice. Wild. Even crazier, she received it all with humility, took great notes, asked dozens of follow-up questions, and very obviously found my thoughts valuable. I didn’t have to do any special research, I just shared what I’ve been soaking in for the last few years. Lesson learned: never shy away from asking “the right person” for a few minutes of their time, they might just enjoy it more than you do.

10/17/24

204. How to offend someone at a networking event: ask 0 questions.😐

205. Last week I met someone and enjoyed learning about their story/background. Then they said “It was great to meet you,” shook my hand, and walked away. What?? Maybe they had another meeting. Maybe I said something that bothered them. Maybe they were just tired. I have no idea, but what I do know is that I left the conversation feeling disrespected & disappointed. I’m bummed to have had this experience but am grateful for the reminder to see and honor the people around me, no matter how busy I may be.

206. Texting is magic.📱

I’m learning most business leaders are ridiculously behind on email at pretty much all times (no matter how hard they try). Texting for the important stuff helps a lot.

207. Definitions matter.🧾
What does the word “traction” mean to you? How do you define “MVP”? Definitions matter, especially for diligence conversations, and after an internal training focused on definitions I’m excited to begin working on a “glossary” of PitchFact definitions for various terms.

10/24/24

208. Deal terms are a sticking point for everyone right now.⚖️
I had like a dozen conversations about valuation this week. Founders: would you rather have a small % of a big pie or 100% of a pie rotting in the trash? Deal terms are regional - what raises just fine on the West Coast will immediately ostracize investors in the South. It’s all about coming into the discussion at a “reasonable” range to start a conversation, otherwise, investors will just be offended and move on to the next deal.

209. NotebookLM is literally insane.🧠

If you haven’t played with this thing, you should. Carve out the time and just do it. I’m currently building like 5 different brains and it’s truly wild how much content this thing can synthesize. Now accepting preorders for AndrewGPT!

210. Speak to the people who care. Way more fun.🎤

I think I blew some minds this week. I gave a presentation to a group of students at Texas A&M University for the Startup Fast Pass program, and one of the things I said was “If you have other stuff to do, that’s fine. I’m here to present to those of you who are interested in this.” Several came up afterward and said this was shocking to them, but it’s something I’ve started saying during a lot of the trainings and volunteer teaching sessions I run. Here’s a link to the full presentation.

10/31/24

211. Don’t be icky.🤢
I had several meetings with warm introductions this week from trusted friends. A couple of them left me feeling “icky”. Why? My counterparty almost immediately asked me for something, and clearly just wanted to talk about themselves. Give first people, give first.

212. Give. Me. The. Nuggets.🍗

Time is truly the most valuable thing someone can offer. Frontload the good stuff. Seeing this play out over and over again the older I get, and this week was no different. BLUF: Bottom Line Up Front.

213. Really hard skill to learn: what NOT to delegate.🛠️

Now that we’ve established a growing team, it’s easy (and very tempting) to just chuck things over the fence. After all, I personally represent PitchFact’s sales, marketing, admin, HR, legal, strategy, corporate development, portions of ops, and general “oh we didn’t think about that but somebody has to do it” team. I’m always stressed. But some stuff, the important stuff, really does need to stay on my plate. What’s important? Good question - welcome to my every waking moment.

11/7/24

214. Building custom automated workflows is stupid easy now.🤖
In the span of 3 hours, I went from zero to a fully automated workflow involving 2 user forms, customized email notifications, multiple database updates, and a series of internal notifications. A few years ago something like this would’ve been functionally impossible for an average yahoo like me. But tools like Claude, PowerAutomate, Jotform, and more have dumbed down the UI so much that us normal folk can build crazy stuff like this in an afternoon. Wild.

215. “Heavy” is relative.🏋️‍♂️

It’s easy to get frustrated with others for being incapable of handling the same load as us. Or that we can’t handle the same load they can. But heavy is relative - it’s unkind and unrealistic to expect someone who hasn't exercised in 3 years to lift as much as someone who never stopped training.

216. Sprinkles and rainbows don’t make you better.🎉

It’s fun to be affirmed, applauded, and celebrated. But that kind of feedback doesn’t really make you any better. This week I reflected on how grateful I am for the people in my life who are willing to point out my shortcomings and walk alongside me as I stumble along.