My 100 Investment Milestone

𝐖𝐞𝐞𝐤𝐥𝐲 𝐓𝐚𝐤𝐞

Most investors measure success by exits and returns. I measure it by what each investment teaches me about recognizing people before they break out.

After making 100 bets on individual talent, certain patterns become impossible to ignore. Some lessons came from wins, others from failures, but all refined my understanding of what separates those who compound from those who plateau.

These aren't abstract frameworks - they're lived observations across dozens of journeys, distilled into the insights that matter most.

𝐌𝐲 𝐈𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭 𝐏𝐫𝐨𝐟𝐢𝐥𝐞

𝐊𝐞𝐲 𝐏𝐚𝐭𝐭𝐞𝐫𝐧𝐬

𝐖𝐡𝐚𝐭 𝐏𝐫𝐞𝐝𝐢𝐜𝐭𝐬 𝐒𝐮𝐜𝐜𝐞𝐬𝐬

Velocity matters more than credentials. How quickly someone learns, ships, and adapts beats any resume. I've backed Stanford MBAs who moved too slowly and community college dropouts who iterated at lightning speed.

Execution beats brilliance every time. A good operator with a decent idea consistently outperforms a genius with poor follow-through. The founder with "bulldozer energy" who pivoted intelligently outpaced the industry expert who couldn't ship.

Energy and adaptability are universal currencies. Founders who bring relentless drive and flexibility find ways through obstacles that stop everyone else. This shows up in how they handle setbacks - they extract lessons instead of making excuses.

Motivation is everything. The founder running toward a mission beats the one running away from a job. You can feel the difference immediately - one radiates purpose, the other radiates desperation.

𝐖𝐡𝐚𝐭 𝐂𝐚𝐮𝐬𝐞𝐬 𝐅𝐚𝐢𝐥𝐮𝐫𝐞

Persistence without feedback loops is wasted effort. I've watched founders grind for years on wrong solutions because they confused stubbornness with grit. The best stay stubborn on vision but flexible on tactics.

Product drift kills more companies than competition. Chasing custom requests before finding repeatability drains capital and morale. One founder built 12 different features for 12 different customers before realizing they had no core product.

Commitment gaps destroy teams. Skills don't matter if one founder is essentially a passenger. I've passed on technically brilliant teams where only half the people were actually working.

Avoid buzzword founders. "AI" or "blockchain" without tangible outcomes is camouflage for lack of depth. The best technical founders talk about problems, not technologies.

𝐓𝐡𝐞 𝐑𝐞𝐥𝐢𝐚𝐛𝐥𝐞 𝐈𝐧𝐝𝐢𝐜𝐚𝐭𝐨𝐫𝐬

The single most consistent predictor: relentless learning. People who turn every win, loss, and pivot into compounding advantage separate themselves from everyone else.

Trust is built in small moments. How a founder handles feedback, setbacks, or ambiguity reveals more than any pitch deck. Character shows up when things don't go according to plan.

Clarity of story equals clarity of thought. If a founder can't explain the value in simple terms, customers and investors won't buy in either. Confusion in communication signals confusion in strategy.

Distribution is harder than product. Great products die without customer access and repeatable sales. Technical edge trumps general capability in complex markets, but you still need to reach customers.

𝐌𝐲 𝐈𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭 𝐑𝐮𝐛𝐫𝐢𝐤

𝐄𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 𝐂𝐨𝐫𝐧𝐞𝐫

𝐐: 𝐖𝐡𝐚𝐭'𝐬 𝐭𝐡𝐞 𝐛𝐢𝐠𝐠𝐞𝐬𝐭 𝐦𝐢𝐬𝐭𝐚𝐤𝐞 𝐟𝐨𝐮𝐧𝐝𝐞𝐫𝐬 𝐦𝐚𝐤𝐞?

They optimize for the wrong timeline. Most founders think in quarters while the best ones think in decades. This shows up in every decision - hiring, product development, fundraising strategy.

The founders who survive the "long, slow middle" are the ones who win. Most ventures die in that grinding phase between initial excitement and meaningful traction. The ones who understand that building something worthwhile takes time are the ones who make it through.

Another critical mistake: confusing motion with progress. I've seen founders who were constantly busy but never moving forward. They mistake activity for achievement, meetings for momentum.

The best founders distinguish between what feels productive and what actually moves the needle. They're ruthlessly focused on activities that compound over time.

𝐒𝐡𝐚𝐫𝐞 𝐓𝐡𝐞 𝐓𝐚𝐥𝐞𝐧𝐭 𝐋𝐞𝐝𝐠𝐞𝐫

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𝐂𝐥𝐨𝐬𝐢𝐧𝐠 𝐓𝐡𝐨𝐮𝐠𝐡𝐭𝐬

You don't invest in what someone is today - you invest in who they're becoming. The most capable people aren't static; they're compounding engines of learning and adaptation.

Most returns come from a few people, but every investment teaches you something about recognizing trajectory. The founder who struggled with their first venture but extracted the right lessons often comes back stronger.

Talent investing isn't about forecasting ideas. It's about recognizing people who turn every experience into fuel for what's next.

Auditing more talent next week,
Will Stringer

𝐅𝐞𝐞𝐝𝐛𝐚𝐜𝐤

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