Get the benefits of real estate, without being an operator. Founder of DealStack. $5M across 30+ private deals of my own. Ex-VC @Techstars, deployed $150M.

Get new deal flow 👉
Joined December 2009
Today's my birthday!! Believe it or not, after 3 years, jet skiing in Miami at sunset was still on my bucket list, and this weekend and my (soon to be wife) Ashley DeMott gifted it to me. I've lived here since December 2023, and it took her booking it for me to actually go. And I will tell you - there's nothing like being on the water when it's warm and the sun is setting, and the wind is in your hair. I don't understand why everyone doesn't live here 😉 It also got me thinking. How many things are on our bucket lists that we could do anytime, but somehow keep pushing off? This was a good reminder to make sure we're actually living. Thanks for taking me out, Ashley.
3
9
394
I am still trying to understand when to use sonnet when coding. Using it for handling the mundane tasks in terms of bookkeeping and taxes. I’m finding this concept of knowing what model to use, when, with what effort… very difficult to follow.
ICYMI we've cut the price of Sonnet 5.5 cache reads in half. In the Claude Platform, it's now $0.10 per million tokens (input is $2, output is $10). This means Sonnet 5.5 now runs ~20% cheaper on most agentic work. (API only, no change to Claude Code usage limits.)
1
1
50
We just launched our newest deal on DealStack: Next Level Blueline Ventures 1. Thank you to Collin Campbell and Chris Larsen at Next-Level Income for bringing it to the platform. There are always a few little bugs when you build something new. But most of DealStack is up and running now, so I'm ready to take on new deals. Listing your deal on DealStack is completely free, and your firm gets its own page that shows up when investors search for you on Google. I'm also giving free distribution to the first 100 firms that join, and 62 have already said yes. So I'd love your help, whether you invest in deals or run them: Reply with a firm whose deals you'd love to see on DealStack. I'll reach out to them personally.
1
48
The 10-year Treasury hit 5.29% last Thursday. That's the highest it's been since 2002. Last October it was around 4.1%. I know, bond yields. Thrilling. But this one changes how I look at every deal in my inbox, so stick with me. 5.29% is what the U.S. government will pay you to lend it money for 10 years. There are no tenants, there's no firm to vet, and you can sell it any day you want. Here's a quick way to see what that does to a private deal. Take the cash yield the deal is promising and subtract the 10-year. Last October, a deal paying 7% was paying you about 3% extra for taking the risk and locking your money up for 5 years. Today the same deal is paying you less than 2% extra. The deal didn't change at all, but the bar it has to clear got a lot higher. Now, I'm not telling you to sell your real estate and buy Treasuries. A Treasury doesn't come with depreciation and it doesn't grow, and a good building can do both. And this could turn around. But it's the question I'm asking of every deal this fall: → What am I getting paid on top of 5%? What's the lowest number you'd say yes to right now?
41
This is insane. I think whether silent or publicly all politicians do this, but not definitely gives me the ick.
BREAKING: President Trump says he will now give a $5,000 “Trump Dividend” to every US citizen if Republicans win the midterms, rather than just US adults. On September 9th, President Trump said that only US adults would qualify for the $5,000 payment. There are ~316 million US citizens, meaning the payments would total ~$1.58 trillion. That is +$350 billion more than the previous proposal.
39
Finally bringing America into the 21st century. I love the focus on ease of use for the American Citizen! 🔥🔥🔥 Oddly, it also makes me feel more proud to be American. 🇺🇸
Chief Design Officer @jgebbia officially unveils America.gov, the new online home for the United States of America
1
53
Ask them if they’d like to go to jail for receiving a commission on the sale of a security without a license. It should clear right up.
Someone introduced me to an investor that they thought I would connect with. After the meeting and the investor was really intersted, the person that connected us called me and said he wants 5% of the raise as an intro fee. That's insane, right?
1
61
Sign me up! Great outdoor vehicle
What if the Semi becomes a multipurpose platform like the Unimog?
2
2
87
Pascal Wagner retweeted
What if the Semi becomes a multipurpose platform like the Unimog?
210
119
38
3,145
139,785
1. Fraud Detection 2. Fraud Detection 3. Fraud D…
What should the IRS ship next?
58
There is alllll this talk about taking a loan out of your whole life insurance policy and using it as leverage in an investment and it makes absolutely NO SENSE TO ME. So many gurus shilling this tool. And to be clear — I’m a big fan of the tool. I get why you’d give yourself a loan and have more control than a bank for short-term needs. But pulling it from your policy and dropping it into a 3–7+ year investment? That’s crazy to me. It may say 3 years. Then it doesn’t exit. Then things go sideways. And you still owe the money. DO NOT DO THIS. Let me illustrate from the last 5 years. 1) You take $50,000 out of your policy and call it 5%. 2) You put that $50,000 into any real estate syndication in 2021. 3) By 2025 you’ve lost the money. Now you didn’t just lose the investment... But you still have to pay $50,000 back to your policy, with compounding interest on top. Probably while other things are going sour too. Now multiply that by however much you decided to pull. I’ve had people come to me what I think about this strategy and if they think it's ok to max out their whole life policy. Let me go on record - that is a recipe for disaster. Not everything you read online is worth doing. Please convince me otherwise. 🙏 OK /rantover
1
49
I don’t like the idea of owning where I live for the simple reason of not wanting to be forced to sell in a down market (like right now) when your life needs change.
58
I'm getting married in 6 weeks!!! What's your biggest wedding day pro tip? Ashley DeMott and I are having a 3-day destination wedding in Marrakech, Morocco. My only regret so far - we capped it at 50 and blew through that almost immediately. Extended family from both sides, plus a few close friends and their spouses. (There are a lot of you I wish were coming, so we'll just need to make up for it when I see you next!) That said, I've been looking forward to this for a year. Practicing my vows. Sorting out the clothes. Finally nailed down the ring. And underneath all of it, I keep landing on the same thought. There have to be things I haven't thought of yet. Plenty of you have already done this and learned something the hard way. Give me your best tip or your biggest learning, so I can go in eyes wide open.
2
2
153
Chris Lopez asked how my $5M+ portfolio is actually invested. So I walked him through it, sleeve by sleeve. Chris had me on the PassivePockets podcast for a solo episode, and instead of talking about real estate deals in the abstract, we went through my own portfolio. A few things we got into: → How I've actually invested a $5M portfolio. → Why I manage separate sleeves of capital depending on whether the money is mine or my mom's. → The asset classes I'm interested in right now, the ones I'm staying away from, and a lot more. My one big takeaway: the same deal can be a yes for one sleeve and a no for the other. Nothing about the deal changed. The job of the money did. Before you look at your next deal, write down whose money it is and the one thing it has to do. Then read the deal against that. This was one of the more fun interviews I've done. I apologize for the quality - I recorded it from Ashley's mom's basement while we were hanging out in Colorado, so not my normal studio setup. If you're interested in passive real estate investing, you'll get a lot out of this episode. Check it out using the link in the comments.
1
44
The full episode with Chris Lopez: how I split capital between my money and my mom's, what I'm leaning into right now, and what I won't touch. youtu.be/hFiv7APxsgY
42
The emotional rollarcoaster of leveraging AI is wild. Some days with AI I am catching lightning in a bottle. I get insane amounts of work done that would have originally taken me weeks or months. Other days, like the last few days, I somehow created a blocker preventing me from accomplishing the simplest of tasks and I start contemplating all my life choices and asking why I’m so incompetent.
26
Pretty interesting take I hadn’t heard before.
What would happen if, say, OpenAI went bust? The doomers will say that's the minute the "bubble" pops. But Google or Microsoft would just buy all of their compute the next morning. Now they've got double the GPUs and they're further ahead than they were the day before. David made a great point in this clip... People keep confusing a financial event with the technology. If someone blows up, the infrastructure doesn't vanish, it just changes hands, and whoever ends up with it will have a lead nobody can close. A bankruptcy wouldn't slow the buildout... it would actually feed it. I've written the whole thing up today, on why the AI buildout cannot stop and where it's all heading. I'll link it below.
35
Pascal Wagner retweeted
What would happen if, say, OpenAI went bust? The doomers will say that's the minute the "bubble" pops. But Google or Microsoft would just buy all of their compute the next morning. Now they've got double the GPUs and they're further ahead than they were the day before. David made a great point in this clip... People keep confusing a financial event with the technology. If someone blows up, the infrastructure doesn't vanish, it just changes hands, and whoever ends up with it will have a lead nobody can close. A bankruptcy wouldn't slow the buildout... it would actually feed it. I've written the whole thing up today, on why the AI buildout cannot stop and where it's all heading. I'll link it below.
50
45
15
399
79,101
Not having a great experience with @bot lately. Making a note for the @grok team. I’ve been struggling with bots just not responding. Help.
1
1
59