EXPERIENCE 003
Show Me What You Saw
Show Me What You Saw
Show Me What You Saw
Venture Associate & Startup Competition Judge
Venture Associate & Startup Competition Judge
Venture Associate & Startup Competition Judge
Evaluating a company means separating the founder’s performance from the founder’s reasoning — and figuring out whether their difference from everyone else in the market came from insight, or just from wanting to be different.
Evaluating a company means separating the founder’s performance from the founder’s reasoning — and figuring out whether their difference from everyone else in the market came from insight, or just from wanting to be different.
Evaluating a company means separating the founder’s performance from the founder’s reasoning — and figuring out whether their difference from everyone else in the market came from insight, or just from wanting to be different.
Evaluating startups can easily become a form of theater. A founder presents for fifteen or twenty minutes, answers a few questions, and leaves — and then a room begins making judgments about who that person is: whether they can lead, whether they can execute, whether they have the kind of conviction that makes other people follow them. I’ve always found that level of certainty a little uncomfortable, mostly because a pitch can tell you something about a founder, but it can’t tell you everything. Evaluation tends to drift toward an American Idol version of business judgment — the room watches the performance and decides, often quickly, whether the person in front of them has “it.” Sometimes that instinct is right. Sometimes the founder is just very good in a room.
Most founders know what they’re going to be asked. What makes you different from your competition? What’s proprietary? How large is the market? Why now? These are useful questions, but they’re also expected, and a polished founder can prepare a polished answer to every one of them well before they walk into the room. The question I find more revealing isn’t “what makes you different from your competition?” Instead, it’s “what makes your competition different from you, and why you decided not to solve the problem their way?” The difference sounds subtle. It isn’t. The first question asks for positioning. The second asks for understanding, because it requires the founder to explain why the market looks the way it does, why competitors chose a different approach, what advantages that approach offers, and what it costs them. More than that, it asks what the founder saw that led them somewhere else — what they rejected, what had to be true for the alternative to make sense, what they noticed in the market or in customer behavior that made another path feel necessary rather than merely available. A company that can answer that is giving me something more useful than a feature comparison. It’s showing me the reasoning that produced the solution, not just the solution itself, and I don’t accept the visible structure of a problem without understanding the logic underneath it.
Some decisions are easier to make than that, though not for the same reasons. A company pursuing a genuine moonshot — a real path toward solving an enormous problem — can make the improbability of the outcome part of the calculus rather than a reason to stop listening, but it’s still a bet on something that may not be possible at all, at any price, on any timeline. The more attractive version of an easy room is the opposite kind of company: one that creates instant recognition by combining things that already exist into a behavior that suddenly feels obvious. Uber didn’t invent GPS, smartphones, digital mapping, or digital payments; it combined technology and behavior that already worked into something that made people wonder why transportation hadn’t already worked that way. That’s a fundamentally better position to invest from than a moonshot. The components are proven. The risk isn’t whether the idea is physically or scientifically possible — it’s whether the company can execute the combination faster and more convincingly than anyone else who could see the same pieces sitting on the table.
Most companies aren’t in either category. They operate in crowded markets, against capable competitors, building products that resemble other products, solving problems that already have solutions — and that’s where evaluation gets harder and where the question behind the question matters most. In a crowded market, being different isn’t enough on its own. What matters is whether the company understands why the market looks the way it does, and whether its divergence comes from insight or just from wanting to make something their own. Those are very different origins for the same-looking decision, and figuring out which one I’m looking at is most of the actual work.
I’ve carried that same question into a few different institutional settings — evaluating applications for the Missouri Technology Corporation’s IDEA Fund, and judging venture challenges and demo days for university entrepreneurship programs — and the settings shape what the answer needs to prove, even when the underlying question stays the same. MTC is public-private capital, so it isn’t only asking whether a company is good; it’s asking whether the company is good for a specific purpose. The fund’s own published figures make that purpose concrete: since 2010, the IDEA Fund has put more than $60 million into over 170 Missouri startups, helping catalyze $2.6 billion in private investment and more than 8,500 jobs in the state. Those two numbers — capital that shows up afterward, and jobs that persist on the ground — are closer to the fund’s real scorecard than any single company’s valuation, which means a company’s divergence from its competitors has to eventually translate into something a state economic-development mandate can measure, not just something that makes a good story in the room.
University competitions run on a different logic entirely, even though the surface looks similar. They aren’t taking equity, and they’re not trying to catalyze a specific dollar figure in follow-on capital — the money is usually smaller, and it exists to buy a company enough runway to survive a hard stretch or reach the point where it can raise a real round on its own. What the program gets back is closer to a halo effect, the reputational credit of having backed something that later succeeded. But the same core question travels intact across all of it: does the story the founder is telling actually agree with the evidence underneath it, and did their divergence from the obvious path come from something they understood that other people hadn’t?
None of that makes the process purely mechanical, and none of it makes it purely a matter of gut instinct either. A scorecard, whatever form it takes, tells you what to look at. It doesn’t tell you whether the pieces underneath it are pulling in the same direction, and it definitely doesn’t tell you whether a founder’s different answer came from insight or from decoration. That’s still mine to work out, every time, before I decide whether the destination makes sense.
Evaluating startups can easily become a form of theater. A founder presents for fifteen or twenty minutes, answers a few questions, and leaves — and then a room begins making judgments about who that person is: whether they can lead, whether they can execute, whether they have the kind of conviction that makes other people follow them. I’ve always found that level of certainty a little uncomfortable, mostly because a pitch can tell you something about a founder, but it can’t tell you everything. Evaluation tends to drift toward an American Idol version of business judgment — the room watches the performance and decides, often quickly, whether the person in front of them has “it.” Sometimes that instinct is right. Sometimes the founder is just very good in a room.
Most founders know what they’re going to be asked. What makes you different from your competition? What’s proprietary? How large is the market? Why now? These are useful questions, but they’re also expected, and a polished founder can prepare a polished answer to every one of them well before they walk into the room. The question I find more revealing isn’t “what makes you different from your competition?” Instead, it’s “what makes your competition different from you, and why you decided not to solve the problem their way?” The difference sounds subtle. It isn’t. The first question asks for positioning. The second asks for understanding, because it requires the founder to explain why the market looks the way it does, why competitors chose a different approach, what advantages that approach offers, and what it costs them. More than that, it asks what the founder saw that led them somewhere else — what they rejected, what had to be true for the alternative to make sense, what they noticed in the market or in customer behavior that made another path feel necessary rather than merely available. A company that can answer that is giving me something more useful than a feature comparison. It’s showing me the reasoning that produced the solution, not just the solution itself, and I don’t accept the visible structure of a problem without understanding the logic underneath it.
Some decisions are easier to make than that, though not for the same reasons. A company pursuing a genuine moonshot — a real path toward solving an enormous problem — can make the improbability of the outcome part of the calculus rather than a reason to stop listening, but it’s still a bet on something that may not be possible at all, at any price, on any timeline. The more attractive version of an easy room is the opposite kind of company: one that creates instant recognition by combining things that already exist into a behavior that suddenly feels obvious. Uber didn’t invent GPS, smartphones, digital mapping, or digital payments; it combined technology and behavior that already worked into something that made people wonder why transportation hadn’t already worked that way. That’s a fundamentally better position to invest from than a moonshot. The components are proven. The risk isn’t whether the idea is physically or scientifically possible — it’s whether the company can execute the combination faster and more convincingly than anyone else who could see the same pieces sitting on the table.
Most companies aren’t in either category. They operate in crowded markets, against capable competitors, building products that resemble other products, solving problems that already have solutions — and that’s where evaluation gets harder and where the question behind the question matters most. In a crowded market, being different isn’t enough on its own. What matters is whether the company understands why the market looks the way it does, and whether its divergence comes from insight or just from wanting to make something their own. Those are very different origins for the same-looking decision, and figuring out which one I’m looking at is most of the actual work.
I’ve carried that same question into a few different institutional settings — evaluating applications for the Missouri Technology Corporation’s IDEA Fund, and judging venture challenges and demo days for university entrepreneurship programs — and the settings shape what the answer needs to prove, even when the underlying question stays the same. MTC is public-private capital, so it isn’t only asking whether a company is good; it’s asking whether the company is good for a specific purpose. The fund’s own published figures make that purpose concrete: since 2010, the IDEA Fund has put more than $60 million into over 170 Missouri startups, helping catalyze $2.6 billion in private investment and more than 8,500 jobs in the state. Those two numbers — capital that shows up afterward, and jobs that persist on the ground — are closer to the fund’s real scorecard than any single company’s valuation, which means a company’s divergence from its competitors has to eventually translate into something a state economic-development mandate can measure, not just something that makes a good story in the room.
University competitions run on a different logic entirely, even though the surface looks similar. They aren’t taking equity, and they’re not trying to catalyze a specific dollar figure in follow-on capital — the money is usually smaller, and it exists to buy a company enough runway to survive a hard stretch or reach the point where it can raise a real round on its own. What the program gets back is closer to a halo effect, the reputational credit of having backed something that later succeeded. But the same core question travels intact across all of it: does the story the founder is telling actually agree with the evidence underneath it, and did their divergence from the obvious path come from something they understood that other people hadn’t?
None of that makes the process purely mechanical, and none of it makes it purely a matter of gut instinct either. A scorecard, whatever form it takes, tells you what to look at. It doesn’t tell you whether the pieces underneath it are pulling in the same direction, and it definitely doesn’t tell you whether a founder’s different answer came from insight or from decoration. That’s still mine to work out, every time, before I decide whether the destination makes sense.
Evaluating startups can easily become a form of theater. A founder presents for fifteen or twenty minutes, answers a few questions, and leaves — and then a room begins making judgments about who that person is: whether they can lead, whether they can execute, whether they have the kind of conviction that makes other people follow them. I’ve always found that level of certainty a little uncomfortable, mostly because a pitch can tell you something about a founder, but it can’t tell you everything. Evaluation tends to drift toward an American Idol version of business judgment — the room watches the performance and decides, often quickly, whether the person in front of them has “it.” Sometimes that instinct is right. Sometimes the founder is just very good in a room.
Most founders know what they’re going to be asked. What makes you different from your competition? What’s proprietary? How large is the market? Why now? These are useful questions, but they’re also expected, and a polished founder can prepare a polished answer to every one of them well before they walk into the room. The question I find more revealing isn’t “what makes you different from your competition?” Instead, it’s “what makes your competition different from you, and why you decided not to solve the problem their way?” The difference sounds subtle. It isn’t. The first question asks for positioning. The second asks for understanding, because it requires the founder to explain why the market looks the way it does, why competitors chose a different approach, what advantages that approach offers, and what it costs them. More than that, it asks what the founder saw that led them somewhere else — what they rejected, what had to be true for the alternative to make sense, what they noticed in the market or in customer behavior that made another path feel necessary rather than merely available. A company that can answer that is giving me something more useful than a feature comparison. It’s showing me the reasoning that produced the solution, not just the solution itself, and I don’t accept the visible structure of a problem without understanding the logic underneath it.
Some decisions are easier to make than that, though not for the same reasons. A company pursuing a genuine moonshot — a real path toward solving an enormous problem — can make the improbability of the outcome part of the calculus rather than a reason to stop listening, but it’s still a bet on something that may not be possible at all, at any price, on any timeline. The more attractive version of an easy room is the opposite kind of company: one that creates instant recognition by combining things that already exist into a behavior that suddenly feels obvious. Uber didn’t invent GPS, smartphones, digital mapping, or digital payments; it combined technology and behavior that already worked into something that made people wonder why transportation hadn’t already worked that way. That’s a fundamentally better position to invest from than a moonshot. The components are proven. The risk isn’t whether the idea is physically or scientifically possible — it’s whether the company can execute the combination faster and more convincingly than anyone else who could see the same pieces sitting on the table.
Most companies aren’t in either category. They operate in crowded markets, against capable competitors, building products that resemble other products, solving problems that already have solutions — and that’s where evaluation gets harder and where the question behind the question matters most. In a crowded market, being different isn’t enough on its own. What matters is whether the company understands why the market looks the way it does, and whether its divergence comes from insight or just from wanting to make something their own. Those are very different origins for the same-looking decision, and figuring out which one I’m looking at is most of the actual work.
I’ve carried that same question into a few different institutional settings — evaluating applications for the Missouri Technology Corporation’s IDEA Fund, and judging venture challenges and demo days for university entrepreneurship programs — and the settings shape what the answer needs to prove, even when the underlying question stays the same. MTC is public-private capital, so it isn’t only asking whether a company is good; it’s asking whether the company is good for a specific purpose. The fund’s own published figures make that purpose concrete: since 2010, the IDEA Fund has put more than $60 million into over 170 Missouri startups, helping catalyze $2.6 billion in private investment and more than 8,500 jobs in the state. Those two numbers — capital that shows up afterward, and jobs that persist on the ground — are closer to the fund’s real scorecard than any single company’s valuation, which means a company’s divergence from its competitors has to eventually translate into something a state economic-development mandate can measure, not just something that makes a good story in the room.
University competitions run on a different logic entirely, even though the surface looks similar. They aren’t taking equity, and they’re not trying to catalyze a specific dollar figure in follow-on capital — the money is usually smaller, and it exists to buy a company enough runway to survive a hard stretch or reach the point where it can raise a real round on its own. What the program gets back is closer to a halo effect, the reputational credit of having backed something that later succeeded. But the same core question travels intact across all of it: does the story the founder is telling actually agree with the evidence underneath it, and did their divergence from the obvious path come from something they understood that other people hadn’t?
None of that makes the process purely mechanical, and none of it makes it purely a matter of gut instinct either. A scorecard, whatever form it takes, tells you what to look at. It doesn’t tell you whether the pieces underneath it are pulling in the same direction, and it definitely doesn’t tell you whether a founder’s different answer came from insight or from decoration. That’s still mine to work out, every time, before I decide whether the destination makes sense.