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From Employee #11 to $100M+ AUM: My Journey from Startup Operator to Syndicate Lead

There's no single path into venture capital. This week I'm sharing mine: how I, Alex Pattis, went from startup employee #11 to managing $100M+ across 400+ deals.

This is part of our ongoing series profiling how different GPs and syndicate leads broke into venture—each taking their own unique route.

Let’s get into it…

First Startup, Employee #11

No ivy league school or family connections into VC for me. My journey began in the trenches of early-stage startups, where I spent 8 years learning the realities of building companies from 0-1.

My first real startup experience came as employee #11 at a company generating less than $1 million in revenue. We had just two customers. As the person leading business development and sales, it was a great opportunity to “figure-it-out” and try to lead efforts to find product-market fit, navigate enterprise sales cycles, and grow revenue.

The experience taught me to appreciate the challenges that founders/early-stage companies face daily: managing cash flow, hiring the right people, and constantly iterating based on market feedback. I cannot stress enough how unique this stage of business is.

2nd Startup, Employee #1 (Pre-Launch)

The lessons from that first startup proved invaluable when I joined my second company, Market Access Transformation, as employee #1 pre-launch. This was even more raw—just an idea, conviction, and vision.

Leading business development and sales from day zero through PE funding five years later, and eventually to a multi-hundred million dollar exit, gave me a front-row seat to the complete startup lifecycle. I witnessed the messy reality of going from concept to customer validation, initial traction to scalable growth, and finally to a successful exit.

These eight years in the startup trenches weren't just about learning business fundamentals—they were about seeing what actually happens when you're building from zero. Every startup is chaotic in its own unique way.

This operator experience became my bridge into VC. I could authentically relate to founders grinding through those pre-Series A challenges because I'd lived it myself.

The Angel Investing Bridge

While still operating at my second startup, I dipped my toes into angel investing. I started sourcing direct deals for small checks and joined syndicates to expand my deal flow and learn the ropes. It wasn't perfect—I was flying solo without seeing how institutional diligence actually works—but I relied on intuition and networked relentlessly to meet as many VCs as possible.

Joining syndicates was transformative. Suddenly I had access to deals I'd never see on my own and could participate in rounds too large for my individual checks. More importantly, I was learning from experienced syndicate leads and investors.

Then I made what seemed like a counterintuitive move: I started sourcing deals for VCs I'd recently met. Why would I send my best opportunities to other investors?

By sharing quality deal flow with VCs, I built real relationships with partners at respected firms, learned their investment processes firsthand, and proved I could identify promising opportunities. The VCs got value, and I got something invaluable—genuine connections built on mutual benefit.

Looking back, this was obvious. I was trying to break into VC with no traditional background. You can't just ask for favors without bringing value to the table.

Leveraging My Unique Skill Sets

The transition from sales and business development to venture capital might seem like a leap, but the core skills that made me successful in closing deals and generating leads became assets in the venture world. My experience in lead generation naturally evolved into an approach to networking that opened doors throughout the startup ecosystem. I was using a similar playbook to building relationships with founders, fellow investors, and industry experts. The same persistence/hustle and relationship-building techniques that helped me fill my sales pipeline became invaluable for sourcing deal flow and building the trust necessary to gain access to competitive funding rounds. 

Securing allocations in oversubscribed investment rounds required a similar approach I'd honed in product sales. Just as I had to navigate complex decision-making processes and build consensus among multiple stakeholders to close deals, I now applied those skills to positioning myself and my fund/syndicate as a great investment partner for the cap table. 

Lastly, leveraging my business development experience at 0-1 stage was a value prop to many early-stage founders. Lots of early-stage founders are brilliant technologists or product visionaries but lack the structured sales and partnership development experience needed to scale their businesses. My background was unique versus most others on the cap table allowing me to provide guidance in building sales processes, crafting go-to-market strategies, and establishing strategic partnerships. 

Grabbing the Bull By The Horn: Running My Own SPVs

After about a year of angel investing and sourcing deals for VCs, I felt ready to take the next step… running my own SPVs. This transition was greatly supported by meeting Bryan Rosenblatt, who became an invaluable mentor to me during this phase. Bryan had experience in syndicate investing (and VC) and was generous with his knowledge about structuring deals, managing Limited Partners (LPs), and navigating SPV operations. This provided a great opportunity to learn the intricacies of SPV management that go far beyond just identifying good deals. 

I began sourcing deals directly and working with LPs to assemble SPVs for direct investments. The accountability was both challenging and motivating—it pushed me to develop more rigorous processes and to think more strategically about portfolio construction and deal resonation with my growing LP base.

Networking became a critical component of growing the business. I spent significant time building relationships with potential LPs, understanding their investment criteria, and demonstrating the value I could provide, primarily through deal access. The LP base grew steadily over the years, largely due to consistency of deals. Staying consistent with high quality deals is one of the best LP growth flywheels in my opinion.

The Current State of My Role in Venture

As of writing this, I've had the privilege of running over 400 SPVs and investing more than $100M through active SPV management, partnerships with other syndicate leads, deal sourcing for VCs, and co-syndication opportunities. I think this is a product of a very aggressive half decade of continuously trying to source the best deals and acquire new LPs interested in our deal flow. This reflects a non-stop networking and collaboration mentality. This is the evolution over 5-6 years of actively deploying capital via SPVs.

Writing small personal angel checks to now managing $100M+ AUM didn't happen overnight. Each deal taught me something new about market dynamics, founder evaluation, or investment structuring. Each LP relationship deepened my understanding of what investors look for in opportunities.

What's particularly rewarding about this SPV model is the collaborative nature which I view unique to traditional VC firms that lead rounds. Rather than competing solely against other investors, there's tremendous value in co-syndicating deals and building a network of trusted partners. Some of my best investments have come through relationships with other syndicate leads who shared interesting opportunities, and some of my most successful deals have been ones where I've brought in co-syndicate partners and/or friendly VCs who added value beyond just capital.

My journey from early startup operator to managing syndicate investments was neither planned nor predictable, but it was built on a foundation of operational experience, continuous learning, and a genuine desire to help entrepreneurs succeed. For aspiring VCs, the key is to start where you are, use what you have, and do what you can—the path will emerge as you take the first step.

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