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I build innovation programs from zero, I build the teams that follow me from one to the…
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Tim W. posted thisEveryone remembers the dot-com crash as a story about insane valuations. I was there for the cleanup, and I don't think that's what it was. I joined the Marine Corps in 1996 and got out in February 2001, eleven months after the peak. I missed the whole boom. What I walked into instead was the wreckage: failed investments stacked up everywhere, companies being rolled up, and capital that had gone in on diligence barely deserving the name. The valuations were the symptom. Nobody checking was the disease. So I've been trying to work out whether we're doing it again. The honest answer turned out to be more interesting than yes or no. Last quarter, investors put 300 billion dollars into roughly 6,000 startups worldwide. Four companies took 188 billion of that. Sixty-five percent of all venture investment on earth, going to four names. That is the part nobody seems to be saying out loud. In 2000, the exposure was spread across thousands of companies, which is exactly why the correction reached all of them. Today it's stacked in a few places and thin everywhere else. That's a different kind of fragile, and it doesn't break the same way. So I don't expect a 2000-style crash. I expect a sort. A great many undifferentiated products quietly absorbed or shut down, with the teams behind them bought for talent, while capital keeps flowing to a small number of companies for years. And I don't think investors are the ones who get hurt most. I think it lands on operators who spent years selling execution, at the exact moment execution stopped being scarce. What part of your work can a prompt genuinely not do yet? I'm asking seriously.
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Tim W. posted thisThe real test of a culture isn't how a team performs when things are going well. I've built and led teams across multiple companies now. The thing I'm proudest of isn't a valuation or an exit. It's that the same people kept showing up. When I started the next thing, they came with me. Some of them have been with me through more than one of those, over many years. I want to be clear that this isn't a soft topic. Culture is the highest-leverage thing a leader actually controls. A team that believes in the work and trusts the person leading it will work harder, longer, and faster than any incentive plan will ever buy you. And the results don't add up, they compound. The same people, same headcount, same budget, produce a different order of output once they genuinely want to be there. I've seen that swing both ways, and the difference is not small. That doesn't come from perks or a values poster in the break room. Looking back, three things did most of the work. Give people the actual problem, not the task. The fastest way to lose good people is to hand them a spec and keep the thinking for yourself. Hand them the problem, the constraints, and the reason it matters, and you find out what they're really capable of. Most leaders are surprised, and most of them waited too long to try it. Take the hit in public, give the credit in public. When something failed, it was on me in the room where it mattered. When something worked, it was theirs, by name, in front of the people whose opinion of them counted. A good leader rewards their people before themselves, every time, and not just with credit. If you take yours first, they notice, and you do not get that back. That trade costs a leader almost nothing and buys years of loyalty. Tell them the truth early, especially the bad version. Every team I've run knew when we were behind, when money was tight, when a deal was slipping. People can carry hard news. What they can't carry is finding out you knew and let them plan their lives around a version you knew wasn't true. Then comes the part nobody puts in the culture deck. Culture doesn't get tested by a bad quarter. It gets tested by money. The day there's enough of it on the table, you find out what was real. Some of it holds and some of it doesn't, and the split is almost never where you expected it. Here's what I've learned from both sides of that: the culture that holds isn't the one with the best stated values. It's the one where people got treated well when there was nothing in it for anyone. If you're building something right now, that's the part worth investing in early, because you can't retrofit it under pressure. And it is not charity. It is the cheapest performance lever you will ever have. Who's the person you'd follow to the next company, and what did they do to earn that?
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Tim W. posted thisA founder I was talking with recently had a single family office ready to put eight figures to work at the seed stage. Not a fund. One family. That's not how this used to work. For the five years I spent building companies at this stage, private offices weren't interested. It was a no every time. Nothing about the pitch has changed since then. The capital above me did. Around 70% of family offices are now active in direct investing, and in June, seed and Series A made up more than a third of all their tracked deal activity. Institutional venture pulled back from the earliest rounds, and family capital moved into the space that opened up. Here's what usually goes unsaid. Most family offices are small. A handful of people, sometimes fewer. So a lot of very lean teams are now looking directly at early stage deals without the research infrastructure a fund would have. Then something else happened. AI made it trivially easy to produce a pitch. Every deck that lands now is well structured, well written, and well designed. The polish that used to signal a serious founder is just the floor. Several people have told me the same thing in different words: it's getting harder to tell what's real and what's a recycled pitch with a new logo on it. Read enough of them and the specificity disappears. You could swap the company name and almost nothing would change. So AI opened the top of the funnel and quietly destroyed the signal at the same time. If you're deploying family capital into seed, the question stops being "is this a good deck" and becomes "how do I know any of this is real." That's why I think the studio model deserves another look, particularly for smaller offices. Instead of underwriting one deck and one founder, you underwrite an operator and a process that's already killed the ideas that didn't earn their way through. You get multiple shots instead of one. The validation happens before the capital goes in, not after. Traction used to be the entry fee. I think it's becoming proof of judgment. For those of you on the family office side: what are you actually using now to separate real from generated? I'd genuinely like to know, because I don't think anyone has solved it yet.
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Tim W. shared thisFamily Offices Are Warming to Seed. AI Just Made It Harder to Know What They Are Buying.Family Offices Are Warming to Seed. AI Just Made It Harder to Know What They Are Buying.
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Tim W. posted thisIn May 2025 I sat in a courtroom and watched my brother-in-law address the man who killed him. Chris Pelkey was killed in a road-rage shooting in Chandler in 2021. When sentencing finally came, my wife Stacey rewrote her victim-impact statement over and over, and none of it felt right. Then she asked a different question: what would Chris say? He was the most forgiving man in every room. So she wrote his words. And we built the AI to let him say them. Stacey, our partner Scott, and I recreated Chris's face and voice, and Chris delivered his own victim-impact statement. It was the first AI-generated victim-impact statement ever presented in a U.S. courtroom. The judge spoke about it from the bench before handing down the maximum sentence. Then it went global. NPR, CNN, CBS, NBC, ABC, the Washington Post, and Reuters carried it here, the BBC and Sky News carried it in the UK, and it ran worldwide from there, as far as Japan. It's now studied by legal scholars at Duke and Yale. Since then our team has built AI avatars and digital humans, clones of real people, for some of the largest companies in the world. The courtroom is still the one I measure all of it against. A few weeks ago I said I'd start sharing what I've learned building things. This is the one that changed how I think about all of it: the highest use of AI is not efficiency. It's deeply human work that could not happen any other way. We spent weeks getting it right, we kept a human hand on every decision, and we built it for one family, one room, one moment of truth. That's the standard I hold every AI system to now, in boardrooms and everywhere else. If it wouldn't survive a courtroom, it isn't ready. What's the most meaningful thing you've ever seen technology do?
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Tim W. posted thisEarly-stage startup funding can feel like an accordion. The VCs squeeze you down: come back after you've raised from angels or friends and family. The angels squeeze you up: you're already too big for us, you're ready for VC money. And the banks won't touch you at all without revenue and collateral you don't have yet. So you get compressed in the middle, bouncing between all three, burning months and momentum, and raising nothing. I call this stretch no man's land. It isn't only the raise. The day a credit card company learns you're self-employed, the limit that was fine last year gets cut, right when you need the runway most. The system is built to fund people who already have money, not the ones building something new. I haven't just watched good companies stall here. I've lived it. And it's rarely because the business is weak. It's because the founder is pitching the wrong side of the table. The trap is treating funding as a straight line: friends and family, then angels, then seed, then Series A. Real capital doesn't move in a clean line. The stages overlap, and the boundaries are fuzzy and personal. Here's the uncomfortable part: early funding is a who-you-know game. The deck matters far less than the relationships. So the way through isn't to pitch harder. It's to find the people who sit on both sides. The operator-angel who co-invests alongside a fund. The seed VC with an angel or scout program. The banker who lends against a name because someone they trust vouched for you. Their real value isn't the check. It's the warm introduction up the chain when you hit the next milestone, and that's worth more than a slightly bigger check from someone who can only do one round. If you're stuck in no man's land, stop optimizing your deck. Start mapping who has relationships on both sides. Founders: where did you get stuck between rounds, and who got you unstuck?
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Tim W. posted thisMost enterprise innovation doesn't die in the lab. It dies in the budget meeting. For years I've built and run innovation programs inside Fortune 500 companies. The hard part is almost never the technology. It's that innovation gets treated like a predictable line item when it is, by definition, a portfolio of bets. Three things kill more programs than any technical challenge: 1. No appetite for risk. Real innovation means some of it won't work. An organization that needs every initiative to succeed will only ever fund what is already safe, which is not innovation. 2. Immature, underfunded programs. A part-time team, a token budget, and no mandate is not an innovation program. It's a hobby, and it produces hobby results. 3. Finance asking for definitive ROI up front. I understand the instinct. But you can't underwrite a breakthrough the way you underwrite a known cost. If the ROI were certain, it wouldn't be innovation. It would be procurement. The programs that win treat innovation like a venture portfolio: fund a set of bets, set clear go or no-go gates, expect some to fail, and double down fast on the ones that hit. In one recent program, I took a client from 13 candidate use cases down to four funded proofs of concept, each with a clear go or no-go gate. The four that advanced earned their budget. The rest were cheap lessons, not expensive failures. You're not buying a guaranteed return. You're buying optionality on the future of the business. The best CFOs I've worked with get this. They stop asking "what's the ROI on this pilot" and start asking "what's the cost of not knowing." What's the most promising innovation you've seen killed by a spreadsheet?
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Tim W. posted thisI'm going to start sharing some things I don't usually talk about. Over the years I've built companies I was genuinely proud of. Not just for the growth, though we grew fast, but for the culture. Teams that trusted each other. People doing the best work of their careers. That still means more to me than any valuation. I've also watched some of it taken apart. Not by the market, and not because we couldn't execute. By money, and what the greed for it does to people. Here's the hardest thing I've learned: it can all turn on you in an instant. You spend years building trust and value, and it can flip overnight, the moment there's enough money on the table to make someone show you who they really are. I'm not writing this to relitigate any of it. I'm past it. I'm writing it because I learned things the hard way that I wish someone had told me earlier, and because the mindset that got me through is worth passing on. So going forward I'll write more openly here. About building culture that actually holds. About growing fast without losing the plot. About protecting what you build, and yourself, from the greed that shows up the moment something is worth taking. And about the way I see innovation, business, and risk, which I know isn't how most people see it. If that's useful to even a few of you, it's worth writing. More soon. What's a hard lesson you learned building something that you wish someone had warned you about?
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Tim W. reposted thisTim W. reposted thisYesterday we inaugurated the Accessibility Living Lab in our Infosys Indianapolis Tech & Innovation hub sponsored by Infosys Foundation USA to focus on exploring emerging technology solutions that can address Vision, Hearing, Motor and Neurodiverse disabilities. The Living Lab showcases a variety of immersive and interactive solutions to support people with Vision, Hearing, Motor and Neurodiversity based disabilities including the award winning AI powered Infosys Accessibility Platform that is designed to help Enterprises to comply with leading Digital accessibility guidelines and provides a real life immersive and interactive experience. The Living Lab developed by the Infosys Center for Emerging Technology Solutions team was experienced by over 150 delegates that were part of the Infosys Foundation USA Crossroads 2025 event including Teachers, Educational professionals, Professors & research scholars from leading US universities focused on Accessibility. https://lnkd.in/esaDeQB4 https://lnkd.in/e3vUd-Br https://lnkd.in/eSxfx_-G #DigitalAccessibility #iCETS Katherine E. Maloney Amrita Naik Inderpreet Sawhney Anant R Adya Ashiss Dash Anand Swaminathan Rafee Tarafdar Manjunatha Kukkuru Shyam Doddavula Saji V S Ganga Susan Kurian Tim W. Scott Yentzer Shamala Sadananda Jagada Krovvidi Vishwa Ranjan Sushrut Vaidya Arun Kumar Harini Suresh Babu
Tim W. commented on a post
1mo
I went deeper on this one, including what I'd ask a founder if I were the one writing the check: https://www.linkedin.com/pulse/family-offices-warming-seed-ai-just-made-harder-know-what-tim-wales-mp0tc/
Tim W. replied to a comment
1mo
Nitish Vaid - Very true, but not always that easy. It is a distraction from what their mission is, so I always advise trying to strike up a conversation to get their feedback before you are in a desperate state for capital. The issue is, would that be considered a solicitation for investment?
Tim W. commented on a post
2mo
The 1880s model had me written off, Jaime. Technical high school, then the trades as a plumber, no degree. Today I build multi-agent AI systems and advise Fortune 500 boards on innovation. Nothing changed about me. What changed was the doors that opened. That's why this matters: reimagine learning around
each kid, keep a real teacher in the loop, and never close the door on the tech that makes it possible. I remember your vision for Google Classroom and it's amazing to see that vision is now a reality.
Experience & Education
Volunteer Experience
Patents
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Shift Worker Platform
Filed US 2018/0025309 A1
See patentNamed inventor on a filed U.S. patent application for a workforce shift-scheduling platform, part of an international patent family with filings in multiple countries.
Projects
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First AI-Generated Victim-Impact Statement in a U.S. Courtroom
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Co-creator and AI technical lead of the first AI-generated victim-impact statement ever presented in a U.S. courtroom (2025). Working with the family of Christopher Pelkey, I built the AI system that recreated his likeness and voice so he could deliver his own statement at his killer's sentencing. The judge referenced it before imposing the maximum sentence. The project was covered worldwide by NPR, CNN, the Washington Post, the BBC, and Reuters, and studied by legal scholars at Duke and Yale…
Co-creator and AI technical lead of the first AI-generated victim-impact statement ever presented in a U.S. courtroom (2025). Working with the family of Christopher Pelkey, I built the AI system that recreated his likeness and voice so he could deliver his own statement at his killer's sentencing. The judge referenced it before imposing the maximum sentence. The project was covered worldwide by NPR, CNN, the Washington Post, the BBC, and Reuters, and studied by legal scholars at Duke and Yale as a landmark example of AI in the justice system.
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English
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SAE Foundation
Member, Board of Trustees
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Kadima.Ventures
Co-founder & CEO
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Jack McCarthy
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