A hat trick 15 years in the making

Doing something different from my typical format. Three companies I was deeply involved with sold in the first half of this year.

There are no overnight successes.

I’m taking you behind the scenes of how I went from growing up on food stamps to having 3 startup liquidity events in 1 year — and buying 100+ acres with friends to build houses for entrepreneurs.

Hope its useful to you.

For most of my life, my dreams felt too big for someone like me.

I grew up on food stamps with a single mom and a tumultuous home life. Someday I may share the details, but for now, the important context is this: stability was not something I grew up taking for granted.

Money was tight. We moved a lot. Home was complicated.

I don’t talk about this part of my life very often.

Partly out of respect for my mom and sister.

Partly because it’s heavy as hell.

But it explains why I assumed my dreams would stay dreams.

And why this year has cracked something wide open.

I got a startup hat trick — three liquidity events — all in the first six months of 2026.

To be clear, I’m not rich-rich.

These are the kinds of payouts that change your nervous system more than your lifestyle.

They take the edge off and turn risk into leverage.

And maybe that’s why this year feels so strange. It’s not just that three things hit at once. It’s that, for the first time, the work I did years ago is coming back around and giving me the room to build what comes next.

But none of this happened overnight.

This “overnight success” has been at least 15 years in the making.

I studied finance in college because I was tired of being poor and wanted a sure-fire job. But I was not good at it. Like at all. After college I worked as a fund accountant in Boston, crying before work every day because I hated my job. My husband Ryan drove me there every morning in the complete opposite direction from his job at Keurig. We stopped at Starbucks, hoping a hug and $4 latte could prop me up enough to get through the day.

The turning point was when Ryan read The 4-Hour Work Week. He made me read it too, and we hatched a plan to move to Silicon Valley.

I quit my depressing finance job, we moved in with his parents to save money, and I waited tables at the Cheesecake Factory while Ryan worked designing atomic clocks. I was embarrassed but I wasn't turning back.

We had no experience in tech, and we quickly realized no one was going to fly us to San Francisco for a job interview. We had to be there in person. Since Ryan made more money, he kept his job while I leap-frogged us to San Francisco.

I showed up to SF sight unseen with a suitcase, high heels — LOL — and pre-printed resumes. The deal was I had 30 days to get a job and an apartment.

If I did, he’d follow me out.

If I didn’t, I’d fly home with my tail between my legs.

I got a fast bartending job at a god-awful tourist trap in Fisherman’s Wharf and signed an apartment lease on the 28th day. I spent my first night there with a roll of toilet paper I stole from work and a borrowed air mattress, but no pillow or blanket.

I applied to startups and got particularly excited about Sauce Labs. After I emailed my application, I was up late and couldn’t stop thinking about how excited I was about the job, so I followed up at 3 am. The hiring manager, Ashley Wilson, saw the “(2)” in her inbox next to my email and was intrigued by my enthusiasm.

I became the 19th employee as an office manager who would help with finance tasks. I invoiced customers, ordered and cleaned up lunch, helped with fundraising paperwork, worked reception, found us a new office, negotiated the lease, managed the buildout, made the monthly board deck, did booth babe duties at PyCon, tracked cloud infrastructure inventory, made a build-vs-buy calculator that helped close a historic $1M annual deal with Yahoo, and planned the holiday parties.

It was a crazy, formative few years. The stuff of the show Silicon Valley. My boss, the CFO, licked me — and others — at a work party. The VP of Sales threatened that if I didn’t sign his expense report for marketing videos (which had no invoice and no marketing videos) I’d never work again in San Francisco.

Despite the rollercoaster, I loved it.

And in the process, I realized that I was bad at finance but not bad at everything.

I left Sauce Labs and followed a mentor to Hansoft, a Swedish startup trying to break into the U.S. market. It was doomed to fail and we all got laid off six months later. I worried six months wasn’t enough marketing experience to stay in marketing. Ryan was at a three-month bootcamp for data science, so I was the only one earning money. The prudent thing to do would have been to apply to lots of jobs.

But there was only one job I wanted.

Intercom (now called Fin), the new darling of SaaS, was hiring a product marketer. I went all in. My resume was landscape layout and full of bright colors, desperately trying to stand out and maneuver my finance career and into a marketing role. I worked around the clock on the take-home project.

And somehow, I got the job.

On my first day at Intercom there was an analog sign that said, “THERE ARE 81 DAYS LEFT IN THE QUARTER, MAKE EVERY DAY COUNT.” People were taking meetings from the hallway floor. We ate lunch in three shifts to fit at the tiny communal table.

Coming from much less successful startups that blew way more money on dumb parties and lavish amenities, it taught me to separate actual success from status signals.

The level of detail was exhausting — at times infuriating — and the pace of shipping was relentless. While at Intercom, I helped launch Educate and Operator, and learned how to develop products and take them to market.

I also wrote a post for the Intercom blog about how product marketing helps build product. It ranked #1 on SEO for “product marketing” for a few years, which later helped me launch my consulting career, and later led me to co-found Olivine.

After three years at Intercom, we wanted to be back on the east coast. This time it was Ryan’s turn to leap-frog us to New York. We were split on two coasts again while I was miserable at an SF fintech startup that promised I could relocate, so I cut my losses, joined Ryan in New York, and decided to freelance until I got a “real job.”

My freelancing earned $192k in the first year, even though I was way undercharging and had no idea what I was doing. The Intercom blog post was paying big dividends, and I was always busy.

When I got a contract too big to take on alone, I asked Ashley Wilson — the one who hired me at Sauce Labs — if she wanted to join forces. She agreed, and we eventually merged our consulting practices to scale Olivine.

Olivine focused on B2B SaaS: launching products, positioning and messaging, sales enablement, and website work. We worked with ServiceNow, LinkedIn, Zuora, Meta, Mercury, and dozens of cool early-stage startups no one had heard of. At our peak we were doing $2M a year in revenue with 40% margins and no meetings on Fridays.

Then covid hit. Ryan and I were living in a studio in Hell’s Kitchen. Curfew was 8 pm and our neighborhood got boarded up from looting. My client work dried up while everyone tried to figure out how long the world was going to be locked down.

We left NYC to regroup in Ryan’s hometown of Haverhill, MA.

Ashley’s husband Santi was working on a “Salesforce wrapper in Slack.” I rode the lockdown on a small PPP loan and Ryan’s health insurance, and took sweat equity in exchange for helping with positioning, website messaging, the fundraising pitch deck, etc.

They raised a pre-seed round and invited me to join full time, but ultimately I wasn’t excited enough about the product space to stay on with Momentum. The economy was bouncing back, so I stuck with Olivine — now with a taste of the earliest days of a startup and growing hopes to build my own someday.

Eventually Ryan and I gave up our apartment to be digital nomads in Portugal, Austin, and Mexico City. Our new favorite podcast, All-In, was hosting a summit in Miami, which was rumored to be a budding tech scene, so we decided to check it out.

I noticed women on Twitter asking if the summit was just going to be a sausage fest, and decided to pull a ladies brunch together. On a whim, I invited Jason Calacanis, not expecting him to join. But he did. Pics were tweeted, and I was henceforth known at the summit as “Brunch Girl.”

The summit was a blast, and the day after we drove around looking at apartments. We were burnt out from traveling with just backpacks and signed a one-year lease on the spot.

Miami wasn’t what we hoped. It was very top-heavy — mostly already successful founders and VCs who had moved there to live in nice houses, not to build the community.

Trying to find more serious people, Ryan and I did Miami Hack Week in 2023 with Jonah Stiennon, a friend from our Sauce Labs days. We won 1st place and “Best Use of OpenAI” back when it was just the API. The $10k prize money did not exist. It took six months to get hold of the organizer, and he never paid.

Disappointed with the quality of tech meetups, I decided to host an All-In Episode 100 meetup in hopes of meeting more of my people. I DM’d Jason Calacanis and asked if he’d consider live streaming the episode. He said no but offered to retweet my signup form. I decided to think bigger than just Miami and listed a few cities, plus a write-in option just in case.

The signup form went viral, and with help from Ana from the Olivine team, we found ourselves orchestrating meetups in 24 cities.

Round two for episode 125 became 50 cities and 10,000 subscribers. JCal asked me what software tool I was using to pull this off and invited me to come work for him. I assured him no software existed, just elbow grease. Three weeks later, he DM’d me offering a $100k investment if I came to his LAUNCH accelerator.

I started assembling a team, including Ryan. And then we left Miami exactly 364 days after arriving for the place we always wanted to go when we retired: New Hampshire.

In the middle of unpacking, Balaji Srinivasan invested $50k and the accelerator started. We were the runt of the batch, but after six grueling months of fundraising, we closed a $1.6M pre-seed round.

The idea was a meetup platform where brands initiated events — usually free meetups — promoted them, and let the audience step up to host. The value prop was more events, less work, centralized data.

It was called River, and building it was false positives and throat punches all the way down.

We got about 250k users on the platform. Bryan Johnson launched his Don’t Die mission on River with 110 simultaneous meetups around the world. Tim Ferriss celebrated the 10th anniversary of his podcast on River with 154 meetups around the world.

Despite getting huge brands on the platform, revenue just wouldn’t grow.

The product worked. The business model didn’t.

Huge fucking tarpit.

Ryan is the one who had the courage to pivot. I was going to keep white-knuckling it and go down with the ship. The trap of “just one more feature.”

We noticed “social dining” exploding in large tier-one cities. But those brands were all building their own app for their own audience. In July 2025, we launched an experiment called DNNR — pronounced dinner — for creators who already had an audience but lacked the engineering chops to make their own.

A year later, DNNR is a white-labeled dinner club platform that lets anyone with an audience send people out to dinner and build belonging that pays. We’re live with 100+ communities, and we just powered The Free Press Supper Club, which sent 2,000 people out to dinner across 28 cities.

That same month we launched DNNR, we hosted a startup community cookout at our house and met Jeremy Hitchcock, an OG in the New Hampshire startup scene.

A week later, I was telling him about my long-held “retirement idea”: a boutique hacker hotel for tech founders and startup offsites, with people building houses around it.

Jeremy had been thinking about something similar. But he didn’t see it as a retirement idea.

He thought we could do it now.

So we exchanged write-ups, compared visions, and started looking for land.

I’d told dozens of people some version of this idea over the years. Most thought it was stupid.

“Why target such a small market?”

“Sounds cool, but it can’t be done.”

But I’ve spent 15 years watching where tech communities work and where they don’t. I’ve lived in Boston, San Francisco, New York, and Miami. I’ve watched fake ecosystems throw parties around nothing, and real ecosystems form around work, density, trust, ambition, and a few people willing to do the unglamorous labor.

We don’t want to build a scene.

We want to build a place for builders.

That’s Freedom Village: 100+ acres in New Hampshire where entrepreneurs, scientists, operators, families, and friends can live near each other, work near each other, host each other, and build things that would be too hard to build alone.

A place with houses. Ownership. Infrastructure. Neighbors. Skin in the game.

And now it’s happening.

We’ve identified land we’re purchasing. We’re finalizing site plans to submit to the city. And this August, at Freedom Summit, we’ll unveil what we’re building.

I’ll share more details soon, but the short version is this: after years of trying to build community on the internet and around the country, I’ve become convinced that some dreams need land.

For most of my life, I thought real ambition was dangerous because wanting too much felt like a recipe for disappointment.

But the last 15 years have been a long apprenticeship in becoming the kind of person who can hold a bigger dream without flinching.

And New Hampshire is teaching me that some dreams need land.

I’m by no means rich. We had big gaps in our earning years and huge student loans to pay off.

But the edge has been taken off.

And money is not the point.

The point is that, for the first time in my life, the things I’ve been working toward don’t feel scattered and impossible anymore.

They feel connected.

Maybe even inevitable.

All of it is suddenly moving very fast.

And I could not, would not, change it.

Having enough money to buy a house in our own fucking village is cool.

But this is not the finish, it's where the real work starts.

After 15 years in tech and a lifetime of trying to outrun survival mode, I’m finally building the things I used to call a dream.

If you’re interested in Freedom Village, come to Freedom Summit August 20–21 in Manchester, NH. You’ll meet builders across AI, biotech, energy, housing, hardware, startups, and community — and you’ll see what we’re building before the rest of the world does.

And if you know a creator, community, or publisher who'd like to monetize their audience in the coolest way ever, check out DNNR.

✌🏻 Thanks for reading and being a part of the journey.

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P.S. Know someone who could launch a dinner club? Refer them to earn 5%
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