Entrepreneur and operator
San Francisco, CA
Joined June 2007
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Big news: I’m joining Relief as VP of Strategy.
For the past several years at BTC Frontier Fund, I’ve focused on fintech and crypto, investing in the infrastructure behind the future of finance. Now, AI is opening up another way to transform financial services: disrupting the service businesses themselves. Rebuilding their cost structures around AI creates the opportunity to deliver an order of magnitude more value and a far better customer experience.
That’s what excites me about Relief. It’s tackling one of the biggest markets in finance: debt.
Borrowing is how millions of Americans pursue the American dream, from starting a business to buying a home. But when debt becomes unmanageable, it can set off a downward spiral that upends people’s lives. American households owe $18 trillion, yet getting help still means navigating call centers, collection agencies, and paperwork.
Robinhood made investing easy, Chime did the same for banking, and Lemonade for insurance. Relief is doing that for debt, with a bigger vision: becoming the place every American can turn to for a brighter financial future.
Relief is an AI-native services business in an industry built around human labor. Where legacy players grow by hiring more agents, Relief is built to scale through software, changing the economics of how many people we can help and how quickly we can reach them.
And it’s working. Relief has already attracted more than 200,000 users, helping people navigate billions of dollars in debt. This year, the team went from zero to millions in annual recurring revenue.
They’ve done the hard work of building the technology, creditor relationships, and customer trust to turn a big idea into a growing business. I’m joining to help accelerate that growth through expansion, new verticals, and investor relations.
I see a clear path from millions to nine figures in recurring revenue by helping more people regain control of their financial lives. That combination of business potential and human impact is why I’m excited to get to work.
If you work in consumer credit or debt, or invest in the space, I’d love to connect.
Follow @startrelief and help us bring a simpler way out of debt to more people.
The logical gap is assuming that earning a follow-on guarantees access
An investor could be the company’s most helpful backer and still get squeezed out by the new lead
Pro rata rights protect against that disconnect between contribution and leverage
Answer: pro rata without the right.
@Neo ditched long-term pro rata rights last year, and we still do big follow-ons in our winners.
We just have to earn each allocation by being good partners rather than resting on an entitlement.
You catch more flies with honey than vinegar!
Pro rata is not just about economic upside, it's also about protecting early investors from dilution
I get the argument that it doesn't incentivize participation and support if the investors already have an allocation locked in
I just think it's wrong
Even the best investors, by and large, do not add much value and taking away pro rata isn't going to change that
Investor have the incentive to help their portfolio raise the next round, regardless
Taking away pro rata just makes the economics of investing early worse
When it's only going to get harder and harder to invest early and get returns
There's going to be 100x more founders and people who otherwise wouldn't have started companies 10 years ago in the game because there's no other jobs
Meaning we need to incentivize more vetting and investing early for the ecosystem to thrive
If you optimize for avoiding conflict in life you will never achieve anything of meaning in this world
Long-term pro rata rights are on the wrong side of history, and can lead to conflict between startup founders and their earliest backers.
We at @Neo decided to ditch long-term pro rata rights: 👇
Now people want to get rid of Pro Rata? 🤦♂️
I think Silicon Valley is underestimating how many ppl are quitting Angel investing past few years because the returns are so abysmal
10 years ago it seemed like Angel investing was the easiest way to make money on earth
Here is an idea:
Let’s take away more and more benefits for the people who are earliest and take the biggest risk in believing in a founder and an idea when others don’t
I’m sure you can see where this is going
Never work with founders who won’t honor pro rata rights
It’s always in service of fucking over the smaller and less influential investors
in favor of the Tier 1s who don’t need it and didn’t earn it
TO retweeted
USDT on Bitcoin. It's coming home
Spent an evening in Washington talking USDT on Bitcoin with @MorganStanley
They invited me to dinner, where I caught up with @MergnerMS, Joe Medioli and a few people from the team I’ve known for quite some time
We talked about @utexocom working with Morgan Stanley on USDT adoption on Bitcoin, both in Europe and globally
TO retweeted
Relief uses agents to manage past-due debt for consumers. It has direct relationships with debt buyers and collectors, partners with the largest debt companies in the world, and connects users with partnered law firms when needed. The average user saves more than 50% of their balance.
TO retweeted
Adam Neumann on why top-down management fails with great talent:
"Top to bottom means you think because someone reports in to you, they have to do what you say."
"But it's not true. This is not a dictatorship. They have free will."
"If you hired someone, they're really talented, they'll go work elsewhere. The more talented they are, the more the top to bottom does not work. They won't be willing to do it. They shouldn't."
"Great talent is not willing to be managed like this."
"If you're gonna manage these employees and you wanna attract the best talent in the world, remember that power comes from influence, not control."
"If you think they need to do what you said because you're their boss, you've already lost, and it's a matter of time till it doesn't work out. If they're okay with it... they're not the right employee for you, and you're not the right boss for them. There's no chance you're getting the best out of them."
@AdamNeumann w/ @StevenBartlett
TO retweeted
Big news for Relief.
I’m incredibly excited to welcome my longtime friend Trevor Owens as our VP of Strategy.
Trevor and I go back more than 15 years to the early NYC tech scene. He’s one of the strongest operators I know, but more importantly, he deeply believes in what we’re building and the people we’re building it for.
Relief has gone from an idea to helping thousands of people navigate billions of dollars of debt, while growing from zero to millions in recurring revenue this year.
But we’re still at the beginning.
We believe financial recovery will become one of the largest categories in consumer finance, and Relief is being built as the AI-native platform for it.
As we scale, Trevor will help us accelerate expansion, develop new verticals, deepen our strategy, and work alongside me on investor relations as we build the next generation of Relief.
The companies that defined the last generation of fintech made investing, banking, and insurance dramatically easier.
Our ambition is to do the same for financial recovery.
And eventually, to become the place millions of people turn when they need a path forward financially.
Couldn’t be more fired up to have Trevor on this journey.
Welcome to Relief, brother. ❤️
Big news: I’m joining Relief as VP of Strategy.
For the past several years at BTC Frontier Fund, I’ve focused on fintech and crypto, investing in the infrastructure behind the future of finance. Now, AI is opening up another way to transform financial services: disrupting the service businesses themselves. Rebuilding their cost structures around AI creates the opportunity to deliver an order of magnitude more value and a far better customer experience.
That’s what excites me about Relief. It’s tackling one of the biggest markets in finance: debt.
Borrowing is how millions of Americans pursue the American dream, from starting a business to buying a home. But when debt becomes unmanageable, it can set off a downward spiral that upends people’s lives. American households owe $18 trillion, yet getting help still means navigating call centers, collection agencies, and paperwork.
Robinhood made investing easy, Chime did the same for banking, and Lemonade for insurance. Relief is doing that for debt, with a bigger vision: becoming the place every American can turn to for a brighter financial future.
Relief is an AI-native services business in an industry built around human labor. Where legacy players grow by hiring more agents, Relief is built to scale through software, changing the economics of how many people we can help and how quickly we can reach them.
And it’s working. Relief has already attracted more than 200,000 users, helping people navigate billions of dollars in debt. This year, the team went from zero to millions in annual recurring revenue.
They’ve done the hard work of building the technology, creditor relationships, and customer trust to turn a big idea into a growing business. I’m joining to help accelerate that growth through expansion, new verticals, and investor relations.
I see a clear path from millions to nine figures in recurring revenue by helping more people regain control of their financial lives. That combination of business potential and human impact is why I’m excited to get to work.
If you work in consumer credit or debt, or invest in the space, I’d love to connect.
Follow @startrelief and help us bring a simpler way out of debt to more people.
TO retweeted
Today, I may have ended my career.
At a time I am heads-down raising our Series B, I did something some people will consider adversarial: I wrote directly to the leaders of America’s biggest banks.
Why?
I was looking through data from the hundreds of thousands of people who have downloaded Relief and engaged with our platform, and what I saw made me sick to my stomach.
Falling behind has become a business model.
Americans have paid billions of dollars a year in credit-card late fees alone. And the people paying those fees are, by definition, often the people already struggling to keep up.
There’s something fundamentally backwards about that.
Relief exists to help people understand their debt, protect themselves, reduce what they owe, and ultimately resolve it. And as we grow, we’re increasingly helping money flow back to creditors that might otherwise have gone uncollected.
So this isn’t an anti-bank letter.
It’s an argument that there is a better model.
Give some of that late-fee economics back to consumers. Give people who are struggling a little breathing room. That money doesn’t disappear. It gets spent on groceries, rent, childcare, transportation, local businesses, and eventually back into the economy.
Banks might make a little less on certain fees in the short term. But healthier consumers are better customers, and a healthier consumer economy is better for everyone.
As Relief becomes larger, I want to make sure we never forget whose side we are supposed to be on.
It’s not always about extracting the maximum dollar.
It’s about treating people like human beings.
And, at the very least, making sure the financial system doesn’t make a difficult moment in someone’s life even harder.
You can try the YC Office Hour Simulator at any Corgi Cafe!
@ycombinator built AI versions of its partners to help more people work through their startup ideas.
For its Office Hour Simulator, the team needed useful answers delivered quickly enough for a spoken conversation. They had been testing lightweight Gemini and OpenAI models before moving to GLM-5.2 on a dedicated Wafer endpoint.
YC then compared that deployment with GPT-4.1 mini on OpenAI and Gemma 4 31B on Cerebras, evaluating answer quality, latency, and conversation duration.
The Wafer configuration delivered 31% lower average LLM latency than OpenAI and 44% lower than Cerebras. Users spent 2.5 minutes longer talking to YC’s AI partners when using Wafer.
Read how YC built the experience and landed on Wafer
🧵 link in thread
Love it
This is incredible. 🔥💦 Real-time battles has arrived in Pokémon Emerald all thanks to a brand new ROM hack. 😮
Read more: retrododo.com/real-time-batt…
More than another cafe? 🤔
Corgi purchased this 9k sf industrial building a few doors down from YC for $11M... gotta be more than another cafe.
Steph Curry paid $8.5M in 2024 to tear it down and build a 25k sf HQ, but scrapped the project after a carpenters union dispute :(
YC opened its new campus a couple doors down that year.
good summary of SF real estate, especially this little submarket.
