On The Cutting Edge Of Entrepreneurship

Thriving at the intersection of startups, career growth, and venture capital

Tom G is a mentor with BeenThere and current student at Columbia Business School. After undergrad at Georgetown, Tom held roles at startups like FiscalNote and Capsule. During his MBA, he’s both working in venture capital roles (Dorm Room Fund and Rucker Park Capital), and building his own startup, onejob, which seeks to accelerating careers by surfacing under-the-radar jobs at top startups along with back door ways to apply.

You started out at FiscalNote. Can you share a little about that role?

Sure! When I joined FiscalNote, they were a team of about 40 people operating out of Facebook’s old office in DC (there was a crazy David Choe mural that FB left behind) and their goal was to make government more transparent through technology. I had been introduced to the founder through my work at Youth Voices, a non-profit I founded to train students to run for public office.

I came on board in a business development role to help start their New York office and over the next couple of years the team grew to 200+ (the team is now much bigger, they bought one of D.C.’s most prominent political newspapers, and they expanded internationally). I learned some business basics (my whole family is in academia), learned how to operate at an early stage startup, and made some incredible friends who have gone on to be founders, VCs, and executives elsewhere.

Pre-MBA, you were a Founder’s Associate / Chief of Staff at Capsule. Those types of roles have seen a lot of traction recently. Can you share more about what that experience is like?

Chief of Staff at startups roles are very much in-demand at the moment, but when I first started looking for one at the tail end of my tenure at FiscalNote, the role was pretty rare. I knew that I wanted to apprentice under a founder, though, and had been following Capsule since it launched because of the massive potential it had, both in terms of business opportunity and impact. I initially applied to a business operations role and was actually rejected for that role because I was too junior — they were looking for 5 years of experience and I had 2 — but I ended up talking my way into a meeting with the CEO and convinced him to hire me.

When I joined, there were 15 of us sitting inside the pharmacy and we didn’t even have desks for everyone. I worked on everything from running our planning and OKR process to managing internal communications to helping to develop our main customer acquisition channel. Eric’s an incredibly talented CEO and I was lucky to be able to learn from him and the rest of the team.

Chief of Staff roles can vary wildly, ranging from executive assistant-level roles to de facto COO to everything in between. I’ve met a bunch of them through the Chief of Staff Tech Network and have helped founders hire quite a few through my newsletter onejob. The advice that I give to founders is to make sure that you’re ready to give responsibility (slowly is fine) to the person you hire, that you have time to nurture the relationship, and that you’ve scoped the role as clearly as you can. To folks who want to be Chiefs of Staff — do your diligence on the company and the founder, understand that you’re working in service of both the founder and the company as a whole, create structured goals and timelines with attached metrics so that you know what you’re accomplishing each week, and make sure that you keep one eye on the horizon — whatever you want to do longer term.

What informed your desire for an MBA? How did you go about deciding on schools to apply to?

I had no formal business training at all. In my household, with a minister-turned-philosophy-professor father and an academic book editor mother, we were much more likely to discuss Kant, liberation theology, or academic politics than anything related to the business world.

Eric, the CEO of Capsule, had gone to business school and always told me how valuable the experience had been for him. As I reached the two year mark at Capsule, it started seeming like the natural next step. My wife and I decided to apply to business school at the same time, so we narrowed it down to three schools based on the quality of the programs and cities we wanted to live in. We were living 20 blocks away from Columbia and we love New York, so we were excited to get to stay in the city and study at CBS.

What do you did well in your MBA application process? What advice would you share with prospective applicants?

One of the things that worked out well for me was only applying to only three schools. Unless you’re absolutely set on going to business school, being honest with yourself about where you’ll thrive and adjusting your focus accordingly will reduce the amount of work you have to do. As far as advice goes, I’d say: definitely do your research on the schools you’re interested in and talk to students, admins, faculty, and other people in the ecosystem. Make sure your essays and resume tell a cohesive story. Finally, be honest with yourself about where the weak points in your application are (GMAT? Essays? Recs?) and budget extra time to make those as excellent as possible. Half of successfully applying to business school is being a diligent project manager, so make sure you have a plan and stick to it.

You founded onejob during your MBA at CBS — tell us a little about founding that and your plans.

During my time at Capsule, a bunch of friends started reaching out to me about transitioning from their banking and consulting jobs to roles like mine at startups. At first, I’d connect them directly to founders that I knew that were looking to hire people. Eventually, it made sense to start a listserv to send out roles that I heard about to everybody that was interested.

The problem with some of the best roles at startups (like Chief of Staff, business operations, GM, etc.) are that they’re often not publicly posted, and if they are you may be one of hundreds of resumes that get submitted. Eventually, I came to see onejob as a way to surface those under-the-radar opportunities to top candidates and give them a back-door way to apply. When I started posting more regularly, word-of-mouth growth kicked in and the newsletter has been growing at 30% month-over-month for the past year. I launched a premium version in January to help active job seekers find more opportunities and have subsequently launched a couple of vertical career newsletters in fintech and healthtech.

I talk to every new subscriber and what I started hearing was that getting a great job is only the first step along a difficult path to achieving your career goals. Once you get the job you have to succeed in it, continually learn new things, build a network of peers with similar goals, find mentors to support your journey, and have the resources to take that next step, whether it’s starting a company or ascending to the C-suite.

Because those additional steps can be so difficult, many people who want to build things end up not fulfilling their potential, which is a loss for them and for society as a whole. So we’ve launched something to help people accelerate their careers along all of those dimensions — it’s in stealth right now, but subscribe to onejob if you want to hear more in the next few weeks.

How about your involvements with Rucker Park Capital and Dorm Room Fund? What led you to these? How have they fit into your schedule next to CBS life?

When I was at Capsule, I found myself spending nights and weekends meeting with founders to see how I could help them, whether by helping them make a key hire, talking through business strategy, or connecting them to sources of capital.

After starting at CBS, I’ve had the opportunity to do that more formally with a few different VC firms, which has been a huge privilege. I’m a Managing Partner at Dorm Room Fund, which is First Round Capital’s student investing arm — we invest $20k checks in student founders and have full ownership over the investment process and also the support of the First Round team. My team has been fortunate to back some incredible startups already; teams building everything from drone infrastructure to financial products for vulnerable populations to a platform powering small business owners. A few days ago, I started working with the team at Rucker Park Capital, an early-stage fund in New York that invests in pre-seed to series A rounds.

I feel so lucky to be able to invest, build my company, and learn from everyone else at CBS, all at the same time. It makes for packed days, but I’ve never been so energized — I wake up before my alarm almost every morning excited to get going.

If you’re interested in other mentor’s career paths, check out our previous interviews with BeenThere mentors Mattia, Lauren and Justin, guide to VC recruiting, and other follow-up resources.

For questions on your career search or MBA application, schedule a free consultation with one of our founders, or search and connect with a mentor like Justin by creating a profile on beenthere.mba!