Finding Professional Purpose

When I was at Amazon, I wrote weekly essays on this newsletter for almost a year on entrepreneurial careers. As a former founder who was suddenly climbing the FAANG ladder, these essays were my way of forcing myself to stay tethered to being entrepreneurial.

It was also my way of answering one of my biggest existential questions: knowing what I know now about how hard it is to start a company, how am I going to find my way back to having enough conviction about an idea that I’ll commit 5+ years of my life to it?

A few years later, here I am taking the plunge with Upside. While my essays here explored pragmatic frameworks and analyses on how entrepreneurs get multiple shots on goal throughout their careers, my decision to go all-in on Upside didn’t involve any spreadsheets or analyses. It came from something a bit deeper.

My obsession with the idea for Upside grew because of a feeling that had been lingering, and once I knew what that feeling was, it became obvious that I should go all-in. Despite all the frameworks I’d written about when navigating entrepreneurial careers, there was one thing that I hadn’t written about: professional purpose. 

That feeling was me starting to understand my professional purpose. The first 10 years of my career included doing Venture for America, building my own freelance marketplace startup, working at AWS where I supported thousands of entrepreneurs at scale I couldn’t have imagined, helping thousands of founders with raising money for their startups, and co-founding a venture studio to help more people start companies. 

I always thought that the through-line of all of these legs of my career was that I was a “startups” guy, but that’s not really a purpose to feel strongly about. As my conviction in Upside continued to build and I asked myself why, I realized that there’d been a deeper professional purpose underscoring the things I loved about each leg of my career: empowering professional upward mobility on people’s own terms. This takes a much more expansive view of what being entrepreneurial is than “startups.”

I joined Venture for America because I wanted an onroad to entrepreneurship myself and wanted to create similar opportunities for others.

The thing I loved the most about building my first startup Compass (freelance marketplace for web design projects) was creating opportunities for people to start/grow their own freelance businesses.

At AWS, I loved being able to support entrepreneurs at a massive scale. I was able to personally coach/mentor thousands of founders on fundraising and behind the scenes I managed programs that provided a lot amount of financial support to entrepreneurs.

I co-founded a venture studio because it could give more people an onramp to starting companies.

The common thing that I loved the most about all of these experiences was helping people achieve upward professional mobility on their own terms – whether that be via a high-growth startup, a solo service business, consulting on the side, or anything in between.

This is why I’m so excited about Upside. It’s the highest-leverage way I can imagine fulfilling my professional purpose, using deep hard-earned insights from my entire career to date. I’m pulling some of the most nuanced insights from all of my career experience, which is resulting in a compelling, differentiated approach to a big market inefficiency.

Upside is a referral partnership platform for professional services (think advisors, consultants, freelancers, small service firms). The thesis is that most knowledge workers want to provide professional services to diversify their career outside of a single employer, but the biggest challenge when doing this is getting clients. This is compounded by the fact that most people do not want to publicly market/sell their services. Typical freelance marketplaces aren’t great as they don't give higher-level knowledge workers control of who can access them, how they work with people, and ultimately the direct relationship with the client. Upside solves this by enabling people to build their own high-trust referral networks. They get client referrals from their network (privately), and they can make referrals to others (and get compensated). We’re essentially deconstructing service marketplace infrastructure and providing it as a platform to individuals so they can refer business amongst each other (and we handle all the formal, awkward, and cumbersome parts of this).

I’ve been building a great founding team I trust immensely (Barry Conrad and Max Nussenbaum) who I’ve worked alongside in various ways for a decade, and we’re already seen some career-altering outcomes with our 50+ paying private beta customers (some of whom are now making 6-figures annually via Upside). 

You can learn more at meetupside.com. We’re hiring a founding engineer (NYC-based). Given that referral incentives are core to what we’re building, if you connect us to someone we hire, we'll give you $5k. If you connect us to someone who connects us to someone we hire, we'll give you $1k.

If there are any other ways you’re curious about getting involved, shoot me a reply.