1/23: It’s widely believed that “grit” is one of the most important characteristics of highly successful people. I have an emerging (and controversial view) that the YOLO investing behavior that we’re seeing is directly attributable to a societal reduction in grit. Unpacked:
2/23: Before shouting down the concept, I encourage you to follow my narrative all the way to the end. I’m not trying to criticize well-intentioned and hard-working people. I’m trying to put a framework around a very counter-intuitive behavior that’s recently emerged.
3/23: What is YOLO investing behavior? For those who haven’t been following it, YOLO stands for “You Only Live Once” and it’s being used as a loose justification for pouring a more than comfortable amount of one’s personal net worth into a highly speculative investment.
4/23: There are a class of YOLO investments that the community has glommed onto. Bitcoin, Tesla, Gamestop, AMC, Cannabis, etc. On the message boards you hear statements like “Take a YOLO bet – ruin a Billionaire’s life” and “To the moon”.
5/23: But why are more and more people investing in highly speculative investments with their hard-earned savings? It violates all semblance of normal financial advice and will likely end poorly for a lot of people.
6/23: Some people attribute it to boredom and the lockdowns. Some attribute it to group think and FOMO. Some people blame the stimulus checks and Robinhood. All are probably contributing to the situation but I think “reduction in grit” is the foundational issue.
7/23: To explain “reduction in grit”, I want to lay down the framework for what I think “grit” is. There are dictionary definitions that fall flat (i.e. – Courage, Conscientiousness, Perseverance, Resilience, and Passion). I’ll pose a much cleaner definition.
8/23: What is my definition of grit? It consists of two major components.

Vision: A vision of a future state that one desperately wants to become real

Control: An unwavering belief that one can take actions that will result in the vision materializing

Vision + Control = Grit
9/23: This description of “grit” boils a complex trait into a simple form. For instance, world class athletes have grit because they want to win championships (Vision) and believe that practice plus diet plus exercise will affect the outcome (Control).
10/23: It also applies to Entrepreneurs. They see a better way of delivering a product/solution to a market (Vision) and believe that they can assemble the necessary resources and operationalize their solution to fill the market gap (Control).
11/23: But it also explains why so many talented people dismiss the idea of going into politics. It’s not that these people wouldn’t be able to map out compelling solutions to our societal problems (Vision). It’s that they don’t believe they can affect the outcome (Control).
12/23: So what happens when an entire society starts losing “grit”? Bad things. We’re not living in the 1960s where there was a belief that as a country we could accomplish anything we wanted to and therefore had the “societal grit” to start and finish big projects.
13/23: We’re living in a time where people don’t believe that they can affect the inputs enough to kink the curve on outcomes. As a society we can’t agree on a vision for the future nor do we believe that our elected officials are working in concert to make our lives better.
14/23: It’s much easier for people to project where the current trends are heading than to imagine a world in which we put our country/world on a better trajectory. Climate? Wealth inequality? Working wages? Human rights? Ability to retire comfortably? Healthcare?
15/23: Without Vision and Control, our society is in a “reduction in grit” cycle. Which leads me back to the original premise that YOLO investing behaviors are directly correlated with this trend.
16/23: The environment: A large segment of society feels that no matter how hard they work or how prudently they invest that retirement is going to be impossible. Causes? Student debt. Housing costs. Healthcare costs. And the boogieman of our government printing money.
17/23: So how irrational is it for this segment to roll the dice on high risk/high return investments? How irrational is it if they have the social proof that other people just like them are doing it? How irrational is it when it’s working?
18/23: The alternative is to find places where individuals can rebuild and focus their “innate grit”. Making more capital available to aspiring Entrepreneurs is a solution for some. Fixing our biggest societal structural issues is important for rebuilding grit in the masses.
19/23: But the concept of YOLO investing is understandable in a world where there’s a belief that tried and true investment advice (allocation across cash, bonds, indexed funds, stocks and real estate) doesn’t result in one’s ability to create financial stability in the future.
20/23: But I fear that many of these investors are going to parlay their recent YOLO successes into YOLO failure. Not all YOLO investments are going to play out in the same way that Bitcoin or Tesla has or that short squeezes are shaping up to become.
21/23: And from there, the downward cycle of “grit reduction” will accelerate because even the promise of YOLO investing will be a fantasy (at least the dollars will have gone poof).
22/23: I don’t pretend to have answers but I would truly like to see the grit cycle pull a 180 and return our country to the days when we felt like anything was possible with hard work and focus. It would be great to believe that nothing but good times were ahead.
23/23: But until then, I fully expect YOLO investing to continue. The crowd will celebrate the high risk/high return success stories and mega-stars in the investment community will emerge. And collateral damage will be brushed under the rug and justified as “part of the game.”

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More from @fintechjunkie

26 Jan
1/12: I’ve been asked a lot why there’s so much variance on “valuations relative to traction”. Some companies are getting 100X ARR multiples while others are getting 2X. There’s no simple answer but a big driver is if a company can demonstrate “Multiplicative Momentum”.
2/12: Every talented Investor eventually comes to the realization that Momentum is one of the most powerful forces in the growth (and therefore valuation) of a Startup. Momentum is a very simple Physics concept that ports nicely over to the business world.
3/12: The Physics formula for momentum is: P=MV (Momentum = Mass X Velocity) but the easier way to think about it conceptually is “mass in motion”. In business terms, it matters how large a company is (mass) and how fast it’s growing (motion).
Read 14 tweets
18 Jan
1/10: Do you want to know a little secret regarding how I build conviction during my #startup diligence process? Do you want to know something that I spend time on that many early stage #VCs brush under the rug as silly and unnecessary? Short thread:
2/10: The answer --- I spend time digesting a company’s financial forecast and then review it thoroughly with the Founding team. “Team + TAM rule!” investors think I’ve lost my mind and that it’s a pure waste of time. Hogwash I say. Why ignore a great learning opportunity?
3/10: To set the context, I rarely focus on going forward projections during the first or second meeting because I need to understand the opportunity at a pretty deep level before running through the forecast. More on this here:
Read 10 tweets
13 Jan
1/39: The only way to describe the public markets’ appetite for new Logos is “insatiable”. But why? SPACs vs. IPOs? I’m no public markets expert by any stretch of the imagination but I’m not going to let that stop me from weighing in on what I think is going on. Unpacked: Image
2/39: Simply put, going public is a financing event. It’s just a choice available to a sub-set of all private companies and is an optional step in a company’s journey of becoming a durable and profitable business.
3/39: There are pluses/minuses to being a public company that I don’t plan on addressing in this thread, but it’s critical to internalize that going public is merely a scenic overlook on a never-ending road trip. It isn’t a final destination because great companies live forever.
Read 39 tweets
8 Jan
1/26: It’s hard to produce a 3X+ #VC fund. It’s much harder to do this consistently. Our first 4 funds are mature enough to know where they’ll end up and all of them will handily beat this benchmark. I reviewed our portfolio this morning and jotted down 12 notes. Shared: Image
2/26: Insight 1: It’s more important to be an average investor in a target rich ecosystem than a great investor chasing windmills. It’s been a great decade for #fintech which made our jobs easier.
3/26: The incumbents have been among the most profitable companies in the world and almost every sub-vertical within #fintech was in dire need of modernization. We believe this is still true which is why we’re comfortable with the pond we’ll be fishing in over the next decade.
Read 26 tweets
5 Jan
1/23: One #startup trap to avoid (founders and VCs) is to fall in love with a value prop that can’t be delivered IRL now. Good diligence will surface disconnects but they’re often brushed under the rug by #VCs who believe fixing delivery over time will be fine. Unpacked:
2/23: The foundational reason why this matters from day 1 is that building a franchise of loyal customers is difficult for any #startup to pull off but the challenge is amplified if the #startup has to rebuild its franchise as it scales.
3/23: Broken or unfulfilled promises lead to customer behaviors that have real consequences. Poor ratings and reviews. High customer service costs. High complaint volume. Low engagement. High attrition/returns/cancelations. Low organic growth.
Read 23 tweets
5 Jan
1/23: One #startup trap to avoid (founders and VCs) is to fall in love with a value prop that can’t be delivered IRL now. Good diligence will surface disconnects but they’re often brushed under the rug by #VCs who believe fixing delivery over time will be fine. Unpacked:
2/23: The foundational reason why this matters from day 1 is that building a franchise of loyal customers is difficult for any #startup to pull off but the challenge is amplified if the #startup has to rebuild its franchise as it scales.
3/23: Broken or unfulfilled promises lead to customer behaviors that have real consequences. Poor ratings and reviews. High customer service costs. High complaint volume. Low engagement. High attrition/returns/cancelations. Low organic growth.
Read 23 tweets

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