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Just Chuck Value
3 takeaways from my conversation with pitch deck guru Matt Gore (Optio)
The Diligent Observer is evolving.
After digesting feedback on the 64 posts I wrote every week over more than a year, I’ve decided it’s to move to posting not once, but twice per week.
You may have noticed something special in your inbox yesterday. One of those two posts will be in the form of a podcast where I interview someone smarter than me with a focus on helping angels make better bets. Yesterday’s podcast was the very first.
Going forward, you’ll receive the following regular content from me:
Tuesday: New podcast episode.
Thursday: Written takeaways from that episode (similar to the format of this post).
I’ll also write the occasional ad-hoc post because the Birkman assessment told me I need permission to break my own rules. Those posts will focus on market analysis, DD, particular deals, or other topics relevant to my objective of helping angels make better bets.
What do you think of this new approach? Love it? Hate it? Hit reply and let me know.
Ok, that’s enough context - now on to the good stuff.
-Andrew
Just chuck value into the ecosystem for decades, and then eventually people are like ‘That’s my guy, I want him on the team.’
Today, I’m breaking down 3 takeaways from my discussion with Matt Gore, founder and managing partner at Optio - Strategic Storytelling.
Check out our full conversation + how to connect with Matt here.
The Observer Express
Don’t have time to read the entire post right now? No worries, here are the main points:
You gotta win the winners. Great deals don’t just “show up” - you’ve got to build networks and give away ridiculous value for that to happen.
90% of the time, the pitch is enough. An entrepreneur’s pitch offers a ton of insight into the underlying business and is a great proxy for sales/recruiting ability.
Double-click on those technical founders. Don’t skip over the technical entrepreneur (read: PhD) just because they’re not the greatest salesperson.
1. You Gotta Win the Winners
Differentiated value-add is mandatory for access to the best deals.
Throughout our conversation, Matt highlighted how his experience has shown that the most compelling opportunities generally get to pick their investors, not the other way around. And in that instance, what ultimately drives the decision is the value each investor can bring to the table. For angels, this highlights the importance of two things:
Build a deal flow network. Developing relationships and networks for access to high-quality deal flow is required to have access to the best opportunities.
Bring tons of value. By giving away value over and over again, without asking for anything in return, doors get opened.
So how does Matt think about identifying a great deal?
2. 90% of the Time, the Pitch is Enough
Most of our discussion on “what makes a great pitch” wasn’t really about the “pitch” at all. It was about the quality of the business itself.
Matt helped me see that the pitch serves as a window into what a company is actually doing behind the scenes. Things like the quality of the deck, the confidence with which a speaker presents, their responses to Q&A, and all the other small details tell you a lot about the business as a whole. For example, he believes that 90% of the time, the pitch serves as a “very good approximation of … the founder’s ability to recruit and sell.” This is a massively important skill set for a founder to have, and the quality of a pitch gives us a lot of helpful clues.
Technical founders, however, are a bit of a different story.
3. Double Click on Those Technical Founders
Nine times out of ten, do not tolerate a bad pitch. But if you are going to tolerate bad pitches, I would tolerate them from technical founders.
Give the PhD a second look. For me, Matt’s comments highlighted the reality that brilliant engineers, researchers, and other professionals are often overlooked because they’re poor salespeople. And that’s a mistake.
Final Thoughts
A great pitch is table stakes to successfully raise capital. I’m grateful people like Matt are out there helping entrepreneurs level up this important “window” into their business. Our conversation showed me it’s important for angels to bring (or as he says, “chuck”) huge value, to pay close attention to an entrepreneur’s pitch, and to take a closer look at technical founders.
What Do You Think?
How do you personally go about “chucking value into the ecosystem?”
*I include this section in every post because I’m genuinely curious to hear what you think. I answer every response, so please, don’t be shy!
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Weekly Observations: 3 Lessons Learned
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.
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.
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.
Weekly Links: 3 Things I Found Interesting
Tune in next week for a breakdown of my conversation with the president of one of the largest angel groups in the country.
Until then, thanks for reading - have a great week.
-Andrew
How did I do this week?
About Me
I cultivate flourishing.
I'm also the CEO of PitchFact, where our mission is to cultivate flourishing specifically through efficient and collaborative early-stage diligence. I'm a proud husband, grateful father, and honest friend. My love languages include brisket, bourbon, and espresso.