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From the Federal Reserve to Fund Manager: Colin Gardiner’s Unlikely Journey into Venture Capital

This week we wanted to share another fund managers unique journey into VC, especially since he leveraged SPVs as a way to turbodrive his way into running a venture fund.

The blog post below is written by Colin Gardiner.

There's no single path into venture capital, and from what I can tell, very few straight lines. This is my story of how I went from working at the Federal Reserve to launching my first fund focused on early-stage marketplaces and everything in between.

Starting at the Fed

My journey started in Silicon Valley, but in the most un-Silicon Valley place, the Federal Reserve Bank of San Francisco, where I got my first job out of college. I was fortunate to get to work under Janet Yellen, who would later become the Chairwoman of the Federal Reserve and Secretary of the Treasury. 

I was tasked with reporting and researching on the ultimate marketplace: the US labor market. I was studying supply and demand dynamics at a massive scale, watching network effects play out in real-time. It was a fantastic job that taught me how to do deep analysis with academic rigor.

The "normal" path from the role was to get a PhD at a top-tier university, but being in SF in the early 2000s, I chose a different route, and I wanted to get my hands dirty building in tech.

Learning Marketplaces by Building Them

I jumped into startups and worked my way through the marketplace ecosystem. At JustAnswer, I learned how to acquire millions of users at scale and how to manage and monetize a labor marketplace. At Ancestry.com, I experienced how great products with proprietary data can build strong network effects. At Tripping.com, as the third employee, I learned how to build a marketplace from the ground up and aggregate millions of vacation rentals.

Then came Outdoorsy, where I joined early as the CPO and eventually CRO. We scaled from a small RV rental platform to over $3 billion in RV rentals and raised $150M+. This was where I really learned how network effects compound over time. Every new RV owner made the platform more valuable for renters, and every renter made it more worthwhile for owners. I also learned two valuable lessons about marketplaces. One, we built a SaaS product called Wheelbase that allowed people to manage their RV rental fleets and seamlessly distribute to the Outdoorsy marketplace. Two, we had to create an insurance program and our own product to make the marketplace work and scale.

The first one taught me about why SaaS-enabled marketplaces can be so successful, as you embed deeply into one side of the market, making it sticky. This would be the genesis of my fund thesis around Marketplace+ models e.g., marketplaces + another product. The second one taught me about how to unlock liquidity in a marketplace and about how marketplaces allow for revenue lego blocks, e.g., you can stack monetization strategies once you have the customer relationships. This led to us building Roamly, an insurtech platform that hit $40M+ in gross revenue.

Looking back, this was a formative time where I developed robust pattern recognition about marketplaces and contributed to raising $200M in funding from Seed to SPAC.

Sharing What I Learned

After Outdoorsy hit unicorn status, I started advising early-stage marketplaces. I'd seen so many founders making the same mistakes that killed promising companies, and I wanted to help.

I began writing daily on LinkedIn about marketplace realities. Not high-level theory, but practical stuff: what good unit economics look like, how to solve the cold start problems, when to introduce payments, how to design take rates that work. My following grew to 16,000+ as people shared the content.

This led me to launch the Take Rate newsletter, which grew to 4,000+ subscribers. What began as sharing marketplace knowledge became something bigger: founders started reaching out for advice before they even began fundraising. I was seeing the most promising marketplace companies 6-12 months before they hit most investors' desks.

Getting Into Angel Investing

The natural next step was getting more serious about angel investing. I'd written some personal checks over the years, but now I started systematically investing in companies I advised, usually getting both equity and advisory shares. The founders got capital plus someone who'd actually built what they were trying to build.

But my personal checks were limited. I kept seeing great opportunities that needed more capital than I could provide alone.

Around this time, I also became a scout for Headline VC, which taught me more about how institutional investors think about marketplaces.

I also started the Wannabe Angels podcast with Harry Campbell to interview successful angels and democratize investing knowledge. The podcast grew to over 13K+ downloads and became another way to build relationships in the angel investing community while learning from experienced investors.

The Syndicate Phase

In late 2022, I launched the Yonder syndicate and ran my first SPV. The thesis was straightforward: use my marketplace expertise to invest in overlooked early-stage platforms before they reached the big VCs.

My first deal had about 25 investors, and I kept expanding my network through outreach. Then I co-syndicated a deal with Harry Campbell, whom I'd met through social media. That changed everything. My LP base jumped to over 200 investors after that deal.

It hit me that success in venture works just like the marketplaces I'd been studying—it compounds through relationships and network effects.

My content strategy was working. I did one SPV in 2022, then seven in 2023. The writing and posting drove consistent deal flow.

Autopilot is a perfect example of how this all came together. The founder discovered me through my Twitter content. I wanted to move fast, so I reached out to Alex Pattis from Riverside Ventures (who writes Last Money In) to co-syndicate. We committed quickly, Craft Ventures joined shortly after, and we closed the deal.

The investment has been a standout. Autopilot went from $360K ARR when we invested to over $2M+ ARR in under a year. They're now tracking toward $13M ARR with $800M AUM.

But I kept hitting the same wall. When great deals moved fast, I still needed time to convince LPs on each opportunity. Sometimes, by the time I got everyone aligned, the round was already closed.

Making the Jump to a Fund

After running eight SPVs, I had no plans to launch a fund. But Jack Greco, co-founder of ACV Auctions, kept pushing me on it. "People love your deal flow," he'd tell me. "You're making this harder than it needs to be."

He was right. I kept hitting the same wall: when great deals moved fast, I needed time to convince LPs on each opportunity. People started telling me I was doing SPVs "on hard mode."

Jack finally convinced me I was solving the wrong problem. Instead of trying to get faster at convincing LPs, why not remove that friction entirely?

The solution became obvious: use a fund for speed-critical initial investments, then bring SPVs back for follow-on situations when I had more time and wanted additional capital.

But traditional fund formation looked impossible—expensive legal bills, complicated administration, multi-million dollar minimums just to get started. I figured I'd need to raise $10M+ to make the economics work, which felt completely unrealistic for a first-time fund manager.

Then I discovered Sydecar's Fund+.

Launching Yonder Fund I

Fund+ made it possible to launch without the traditional barriers. Instead of needing to raise $10M+ just to cover expensive fund administration, I could start with $2M and focus on what mattered: finding great companies.

The timing couldn't have been better. The 2022-2023 market reset created a unique window where excellent early-traction marketplaces were available at reasonable valuations—something that hadn't been true since 2008-2010 when companies like Airbnb and Uber were raising their early rounds.

In early 2024, I launched Yonder Fund I with clear parameters: $2M investing $50K in pre-seed and seed marketplaces at sub-$10M valuations. I also offer a co-syndication to my LPs in the form of an SPV. This is a nice structure as the fund can write the anchor check and add additional capital from LPs and other investors.

The early results have been promising. Across the past three years, I've deployed $4.5M in AUM across 36 investments through angels, SPVs, and the fund. Portfolio companies include Autopilot ($13M ARR, $800M AUM, backed by Craft), Packsmith (Bessemer, Interplay, Trust Fund), Throne (Moxxie, Long Journey, Lance Armstrong), and Howie AI.

The fund has completed 14 investments before or alongside VCs like Founders Fund, Norwest Venture Partners, Lerer Hippeau, Seven Seven Six, Mucker, Precursor, and Hustle Fund. Two-thirds of the 2024 cohort have already graduated to their next round, and according to Carta, the fund has an early top decile trajectory based on current markups.

The LP base includes world-class founders from companies like Grubhub, ACV Auctions, Mercari, and OLX, plus operators from Airbnb, Uber, Amazon, DoorDash, eBay, Thumbtack, StubHub, OpenTable, and many other marketplaces.

Why This Actually Works

The key lesson: build something that aligns with your unique edge. Don't try to be everything to everyone.

For me, that's marketplaces. The data backs it up: since 2010, 50% of top VC IPOs came from marketplaces. But marketplace investing is considered "hard." The two-sided dynamics and cold start problems intimidate generalist investors.

That's precisely why it works for me. My 15 years of building billion-dollar platforms give me advantages others can't replicate. I can quickly assess whether a marketplace has real product-market fit, evaluate their customer acquisition strategies, and spot early network effect signals that generalists miss.

The magic happens when your fund thesis perfectly matches your unique edge.

What's Next

I officially launched Yonder Fund I, and everything I've done has led to this point. Working at the Fed gave me analytical frameworks. The operational experience provided pattern recognition. Content creation built founder and investor relationships. The syndicate proved the investment thesis.

Now I'm backing the next generation of marketplace founders who are building new economies. I am excited to build the Fund, but I am more excited to create a Firm that becomes the go-to for early-stage marketplaces.

Want to be part of it? If you are interested in being an LP or are an early-stage founder, don't hesitate to reach out to me at [email protected].

If you enjoyed this article, feel free to view our prior posts on adjacent topics 

• Why Syndicate Leads Don’t Survive 

• The Syndicate LP Churn Problem 

• What Really Drives Investment Interest in SPVs

Last Money in is Powered by Sydecar

Sydecar empowers syndicate leads to manage their investments more effectively. Organize, manage, and engage your investor network effortlessly with Sydecar’s management and communication tools. Their platform also automates banking, compliance, contracts, tax, and reporting, freeing up syndicate leads to focus on securing deals and strengthening investor relations. Elevate your syndicate operations with Sydecar.

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✍️ Written by Zachary and Alex