I posted a tweet that generated a slew of DMs asking me to share specific details.

Wish granted:👇🧵
2/11: The Appreciation

The email intro was complimentary but sincere. The Founder wanted to thank me and the broader QED team for the work we put into diligence and for allowing him to interact with our team. He referred to the process as an “invaluable learning experience”.
3/11: The Apology

The meat of the email was a broad apology. From QED’s perspective the final diligence conversation didn’t go smoothly and it’s obvious from the message that he agreed. And his apology wasn’t generic --- it demonstrated that he knew why it didn’t go well.
4/11: Directly from the email:
5/11: The Secret

The last part of the email revealed the strength of the relationship that we had built during the diligence process. He shared vulnerability and was seeking advice.

The secret was that he was parting ways with his co-Founder and abandoning their business idea.
6/11: The decision wasn’t easy because they had been refining their business plan and pitching their dream to investors for the better part of a year. But their relationship wasn’t merely a business relationship. They had known each other for years.
7/11: He shared that the fundraising process was eye opening and that conversations with people like me helped him make his decision. Over time he concluded that the business he was pitching with his co-Founder was flawed and needed a major overhaul.
8/11: The rub was that his co-Founder wanted to chase the idea as-is. A term sheet from a Tier 1 firm had hit their desks that would give them enough capital to get started.
9/11: Tough conversations with his co-Founder followed. And when it became obvious they didn’t see eye-to-eye, he felt it best to part ways before being stuck to each other and to a professional investor.
10/11: He shared that he would feel extreme regret if he labeled himself as a quitter which is why he made it clear to be that he wasn’t technically quitting. Instead, he was starting his own company and welcomed my guidance if I were willing to help.
11/11: There are many fundamental learnings about human nature and the strength of relationships that Founders and VCs can derive from this situation. But the Bard said it best:

“This above all; to thine own self be true”.

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More from @fintechjunkie

15 Oct
Making decisions when faced with incomplete information is what every Entrepreneur has to contend with on a daily basis. The same is true for Investors.

Curious what role Intuition plays? Curious how Intuition is misunderstood and misused? Read on: 🧵👇
2/22: Making a decision when complete information is available isn’t terribly difficult. Outcomes aren’t guaranteed, but it’s generally true that the more information one has about a situation the easier it will be to map out a productive path forward.
3/22: Of course there’s no such thing as “complete information” so decision makers have to guide their organizations armed only with limited and imperfect information. Great Founders and Investors build conviction and act decisively even when faced with uncertainty.
Read 22 tweets
5 Oct
Nothing is normal anymore. The VC landscape is nuts. Public markets are on fire. The adoption of Web3.0 technologies is unlike anything seen before.

Separating bubbles from mega-trends is really difficult. It’s the stuff of dreams and nightmares. A few thoughts: 🧵👇
2/9: None of us have a crystal ball that can accurately predict what the future holds. But there is less of a difference than one would think between mania and durability. Fleeting interests and beliefs drive mania. Value creation and societal acceptance drive durability.
3/9: It makes me want to re-read a seminal book that was published in 1841 that many see as the “OG” of crowd psychology and mania:

“Extraordinary Popular Delusions and the Madness of Crowds” by Scottish journalist Charles Mackay
Read 9 tweets
30 Sep
Fintech startups have been on a tear for the past decade and some gigantic companies have emerged including @stripe, @nubank, @Affirm and @Klarna.

The question I get asked all the time is: Is there room for the next wave of fintech startups to succeed?

A few thoughts: 🧵👇
2/23: If you were to study any specific financial services product at any point in time, you’d find a few companies dominating that product’s ecosystem. These “incumbents” typically operate with similar business models, products and end-user experiences.
3/23: Some eras are defined by stability where the incumbents trade market share back and forth, but in other eras a small handful of innovators emerge that behave like annoying gnats. Sometimes the gnats go away but sometimes they end up thriving.
Read 23 tweets
27 Sep
Last week was pretty crazy. I knew what was coming first thing Monday morning and the week didn’t disappoint.

A few thoughts on how the VC ecosystem is quickly evolving:
2/22: Anyone who regularly reads my threads has a good understanding of my angst about how the ecosystem has been shifting from “deep diligence and pricing discipline” mode to “FOMO and speed for optionality” mode.
3/22: The speed of this shift is dizzying for those of us who have been around a while. I was talking to a seasoned Investor who commented that he’s seen more change in the past 3 months than in the previous year and more change in the past year than in the previous 5.
Read 22 tweets
24 Sep
Everyone knows the speed at which VC deals are being done has accelerated to a dizzying pace.

While this can be good for some Founders, it’s magnifying a flaw in the VC ecosystem.

A few thoughts on “Bad Pattern Recognition” and how it’s creating have and have-nots: 🧵👇
2/21: 14 years ago I hung up my operating hat to become a Venture Capitalist. Knowing nothing about investing, I sought out seasoned Investors so that I could learn from their experiences. Borrowing a degree sounded like a better strategy than earning one from scratch.
3/21: It shouldn't come as a surprise that much of the advice was generic and in the "no duh" camp. It started to feel like many Investors’ diligence processes consisted of evaluating startups on a laundry list of “generally true” criteria. Ticking the right boxes = Term Sheet.
Read 21 tweets
22 Sep
1/4: Quick observation:

I'm seeing an acceleration of "Keeping up with the Joneses" behaviors in the startup ecosystem.

Founders want to grow crazy fast, raise lots of money, and issue press releases about their valuations so that they're "ahead of their peers".
2/4: VCs care about eye-popping rounds, markups, and backing the market-leading logos so that they're "ahead of their peers".

Systemically de-risking a business over time matters but is being brushed under the rug in favor of more immediate and easier to highlight achievements.
3/4: This isn't a surprise given the industry's reward system and the need to stand out.

For a startup, public vanity metrics help paint the narrative that it's winning. Winning attracts talent. And it's the talent that then helps materialize the narrative into reality.
Read 4 tweets

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