Brianne Kimmel — solo capitalist, founder of Work Life Ventures, and investor in seven unicorns — breaks down how VC economics actually work: management fees, carry, and what solo capitalists can realistically make. She covers how she got first-money-in status on Pipe by texting the founder on her birthday, her Hopin investment (now valued at $5.65B), and the trend of disrupting venture with non-dilutive capital. Shaan opens with a segment on AI-generated voices of dead people (Anthony Bourdain doc, GPT-3 grief companion). Sam and Shaan debate whether elite universities are actually broken.
Speakers: Shaan Puri (host), Sam Parr (host), Brianne Kimmel (guest, founder of Work Life Ventures)
AI Voices of the Dead [00:00:00]
Shaan: There’s a new Anthony Bourdain documentary — Roadrunner — and at the end they have this remarkable sound bite. Right before he died, he wrote an email to someone. Not a suicide note, but something like “I’m sad.” In the documentary, you hear him read it. Except it’s not actually him. He died. A company used AI to recreate his voice from existing recordings and read out the email. If you didn’t know, you’d think it was him.
Then I read about a guy named Josh whose girlfriend died. He took her Facebook messages, texts, tweets, and fed them into GPT-3. He built a version of her he could talk to. A companion who sounds like her, responds like her — but she’s dead.
Sam: Is this wrong?
Shaan: Two questions: Is it wrong to do the Bourdain thing? And when are we going to start talking to our dead moms?
Brianne: The Bourdain thing I actually think is kind of cool — if you’re carrying someone’s story forward, building their legacy. Taking a book written a decade ago and giving it the voice of someone who’s passed — that’s a storytelling tool. The gray area for me is the grief companion. I’m a little concerned about the guy staying in the past instead of going through therapy or getting back out there.
Shaan: There’s already an app called airwriter.app where you can ask Ben Franklin a question. They’ve uploaded his personality from his writings. And somebody trained a GPT-3 model on me from stories I’ve told on the podcast. You could ask it questions and it would answer in a way that sounded basically like me bullshitting.
There’s also a startup using video deepfake to let companies send personalized messages at scale. You record yourself once: “Thanks for leaving that review on iTunes.” Then the AI takes that recording and swaps in the customer’s name at the beginning — “Hey Sam, thanks for…” — making it look and sound personal. I want to invest in it.
Who Is Brianne Kimmel? [00:14:00]
Shaan: Let me read three things off your bio. Solo capitalist — you raised your own fund by yourself after never having worked in VC. Correct?
Brianne: Correct.
Shaan: You’ve invested in seven unicorns already. And you have possibly the most color-coded calendar I’ve ever seen and I just want to know what’s wrong with you.
Brianne: I’m a little embarrassed you saw that.
Sam: The real question is: you went to a state school, grew up in Ohio, worked at Expedia, then Zendesk — you’re a normal person. And somehow you got into seven unicorn-stage companies before you even raised your fund. How?
Brianne: I started as a marketer. I started meeting founders at startups on evenings and weekends. Started hosting dinners. I was intentional about my first few angel investments — Webflow was one. I organized a go-to-market workshop, invited the Webflow team, spent a whole day with them. Hosted no-code dinners. Spent as much time as possible with a handful of companies, found interesting touch points that gave me enough of an angle to invest.
The thing about being in Silicon Valley is proximity matters enormously. You walk into a dinner, make two connections, stay in touch, and everyone there is going somewhere. Nobody moves to the valley and pays insane rent to not be in the mix.
Brianne’s Calendar: The Insane Daily Schedule [00:22:00]
Shaan: Let me just read your Wednesday out loud because it’s remarkable. 7 AM — Morning Block. What happens?
Brianne: I go to the gym.
Shaan: Morning Block Two: 30 minutes, emails to portfolio companies, ways to help. Team check-ins. Email processing. Prep pitch one. Pitch one. Pitch one follow-up. Pitch two prep. Pitch two. Follow-up. Text triage — what’s that?
Brianne: I’m terrible at responding to texts. I’ll read one and think I responded and then reply four days later. I actually block time in my calendar specifically to go through texts. In early-stage venture a lot of business happens over text and phone — it’s highly inefficient compared to corporate. No Slack, no email threads. Just one-on-one texts.
Shaan: Then: virtual dinner, life admin — that was apparently when your driver’s license and passport were both expired — and then Evening Block 8 PM to 11 PM.
Sam — I’m the opposite. My EA’s only job was to make sure nothing got onto my calendar. If someone asked for a meeting, she’d say: “Can he Slack you instead?” And if I asked her to schedule something, she’d say: “Are you sure?” And she’d delete all group meetings for the next three weeks and let me re-add them if they were important.
Brianne: I think the calendar helped because I’m not naturally good at working from home. The structure was useful when building the firm from scratch. Will I do it forever? Probably not.
How VCs Actually Make Money [00:32:00]
Sam: Walk us through the VC money model because I genuinely can’t figure out how money gets into your pocket.
Brianne: So the way most VC funds work: you raise a fund — let’s say $25 million — and you charge LPs a management fee, typically 2 to 2.5 percent of the fund per year. That’s your salary, essentially. On $25 million at 2.5%, that’s $625,000 a year to run the fund.
Then there’s carry. Carry is your percentage of the profits. Standard is 20 percent. So if you invest the $25 million and return $125 million — a 5x fund — you first give back the $25 million to your LPs, then split the $100 million profit 80/20. Your 20% carry is $20 million. That’s your big check, but it comes at the end — year seven or ten.
Shaan: We looked at a crowdsourced spreadsheet of VC compensation — user-submitted salaries and carry numbers from around a thousand VCs. The pattern was: small funds under $100M look like a high-paying job ($250-500K/year base) plus a big windfall if you hit winners. The really large funds — $2B+ — have enormous fees ($40M/year just in management fees) but their expected multiple is lower because you can’t 5x a $2B fund easily.
Brianne: Exactly. And for solo capitalists, the real upside comes from SPVs — special purpose vehicles — on top of the core fund. You set up a one-off vehicle for a specific company, bring in one or two LPs, everyone invests together. The core fund builds your track record. The SPVs are where you can make money in the short term, especially on later-stage companies where there’s still upside.
One thing I encourage people: start small. I raised a little over $10 million for Fund One and returned it on paper in year and a half. That’s a much safer path than trying to raise $100 million immediately and overextending yourself.
Getting First Money Into Pipe [00:46:00]
Sam: Tell us about Pipe. How did you end up as first-money-in?
Brianne: I heard about Pipe on September 10th — two days before my birthday. Friends in LA mentioned this guy Harry Hurst who was building something in SaaS, very charismatic, you’ve got to meet him. I tried to get an intro for two days. Nothing was happening.
On my birthday, I just tracked down his phone number. Texted him: “Here’s who I am, here’s what I do, I’m in LA and it’s my birthday — can I come to your office?” He said let’s meet in the middle, at Soho House. I went, heard the pitch, and committed on the spot. Sitting in the parking lot afterwards on my birthday, laptop out, starting the process to wire money — because I knew if I waited, it wasn’t going to happen. Founders are meeting so many investors. If they don’t hear back fast, they forget.
Shaan: What’s Pipe worth now?
Brianne: North of two billion.
Sam: And you got in at…
Brianne: About $9 million post.
Sam: So your $150K is worth…
Brianne: I don’t do public math. But I will say: that investment returned the fund. On paper, in year one and a half.
Hopin and the Future of Work Portfolio [00:58:00]
Shaan: What’s the biggest hit in your portfolio right now?
Brianne: Hopin is the most obvious. When I first invested, they had four employees. I caught up with Johnny last week — they’re at 820 people. They’re now valued at $5.65 billion.
The founder, Johnny, built Hopin because he had a compromised immune system and couldn’t go to networking events. He built the technology because he needed it. They started as a platform for hosting virtual conferences, then moved into streaming, virtual collaboration, hybrid events. The upside feels uncapped to me.
There are also two other companies in the portfolio I can’t talk about yet. They’re in stealth. But the two themes I’m most excited about: disrupting venture capital itself with non-dilutive capital for founders, and education and reskilling.
Is Elite University Education Broken? [01:10:00]
Sam: You invested in Primer — an online education company. Give us your take on whether education is broken.
Brianne: I invested in Primer because I think we’re teaching kids the wrong things for the wrong reasons. They’re memorizing content, taking the test, forgetting everything. But I’m seeing new platforms that teach kids based on their actual interests — video game design, coding, writing — skills aligned to what they care about.
Shaan: I’ve completely changed my opinion on this. Everyone says education is broken. I now think: only for the schools outside the top 20 or 30. If you could get into a top 20 university — even if you have to go into serious debt — it is 100% worth it.
Sam: I completely agree.
Shaan: Because it’s not about what you learn in class. It’s two things: the stamp — every time Sam or I see Harvard on a resume, we perk up a little bit — and the network. You’re spending four years bumping into the next Zuckerberg in your dorm. Those are the reasons it’s worth it.
The problem is schools like Belmont — $50K a year, nobody outside your city has heard of it, you get the debt and zero of the benefits. Those schools should go out of business.
Brianne: I agree. And the AI-scanning-resumes reality has made this worse. Algorithms at big companies are literally filtering for Harvard, Stanford, MIT. The schools that can’t provide the credential or the network have no value proposition.
Shaan: My dad actually gave me the best advice about this when I called him halfway through my freshman year at Duke saying I wasn’t doing as well as I expected. He said: “You’re not there for grades. You’re there because Tawfiq is sitting next to you and that other guy is across the hall. Just being five feet away from these people is going to make what you consider normal feel excellent, because their baseline is excellent.”
I didn’t understand it at the time. Now I get it. The compounding value is in who you’re surrounded by for four years — not what the textbooks say.
Sam: And the companies trying to “fix” education keep solving the wrong problem. They make a better mousetrap for information delivery. But people don’t go to college for information. They go for the stamp, the social experience, the parental insurance policy. Fix those things, or it’s not really an alternative.
Shaan: Alright Brie — we’re eating into your calendar. Where should people find you?
Brianne: Work Life Ventures — worklife.vc. And The Shake Up podcast with my co-host Alexis Gay, now on the HubSpot Podcast Network.