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Five Burning Questions with Boston-Based Innovators: Justin Whitehead, Co-Founder of Pebble Finance

Justin Whitehead, a computer science major from Upstate New York, has been at the intersection of finance and technology for what he describes as “forever”. He got his start as an engineering intern at Connecticut-based FactSet, a small company at the time that now competes with Thomson Reuters / Refinitiv, Bloomberg, and S&P. After over a decade with FactSet, Justin joined Kensho Technologies, a Boston-based startup that harnesses AI and machine learning to solve the hardest analytical problems in finance. Justin saw Kensho through to acquisition by S&P a few years later, and joined botkeeper as the CTO (he left Kensho’s engineering team in the good hands of his wife Melissa who is Kensho’s current CTO!).

Pandemic 2020 found two CTO parents in what seemed like one endless Zoom call with two children and school schedules up in the air. By the Fall of that year Justin decided to leave botkeeper so he could help the kids through the hybrid school year. He jokingly said he became a kindergarten teacher for that year. This switch freed up the time to reconnect with Kensho alumni Steve and James, and the headspace to come up with the idea of Pebble Finance, a financial platform that gives private investors more control over their portfolios. The band got back together, and I got to catch up with Justin on the day Pebble Finance closed its seed round led by NextView.

Here are Justin’s instructive and funny answers to five questions that may strike the chord with fellow Boston-based cofounders.

What do you wish you knew when you were starting your business?

Tech and product are my jam. Things that took a disproportionate amount of my time were MBA-type of things. For example, I went and did the taxes for the company myself, because we are thrifty, and guess what, that’s a little bit different from personal taxes!

And then there’s quite a bit of learning when it comes to talking to investors. I can talk tech, product and strategy all day long, but there is a new language you will need to learn. Answering questions like ‘Are you B2B or B2C? What’s your LTV to CAC?” was new!

What things you thought would be hard, but they ended up being easy? Payroll, for example?

We don’t have payroll yet. I knew setting up a legal entity may involve a fax machine if you do it yourself, so I think the hardest part was “I don’t own a fax machine anymore, let alone want to hunt for one’. But Gust made a lot of this stuff easy.

Another one: we brought on a contractor and paid her with equity. I thought that was going to be a rigmarole, but Gust made that surprisingly easy. Using Gust early on helped us keep all the company records nice and tidy which was amazingly helpful during the due diligence process for the seed round.

What is unique about Boston startup scene?

I spent a lot of time in the Connecticut startup scene, but also a lot of time in New York. New York has a high concentration of people and industries. Think fintech, adtech, etc., so one of the coolest things was that you could go to a random bar, speak out loud about some problem you were tackling at your company, and you’d find someone within earshot who was interested in what you were doing, and could share their experience with you.

There is a bit less density in Boston, people are more spread out. There is a wide variety of industries but no distinct concentrations unless you’re biotech. So it’s not like you can go to a meetup and find a bunch of people from, say, the fintech or consumer tech industry. However, the available talent in Boston is special. We have these amazing schools and an atmosphere for attracting fresh innovative talent. It gives you access to some of the brightest students in the country.

Additionally, there are the industry veterans who’ve returned to Boston to take advantage of the amenity here. You get access to excellent schools, the mountains and oceans, Cape - you’ve got all these things that are fantastic for raising families. As for building companies you benefit from that mixture of experience and fresh innovation.

Additionally, Boston’s excellent schools, the mountains and oceans, and Cape are attractive for industry veterans who start thinking about raising a family. After having spent their twenties exploring New York and San Francisco the desire to have access to the city without the need to be in the city brings a lot of them to Boston, which creates the mixture of experience and fresh innovation that is fantastic for building companies.

What are 3 trends / developments for entrepreneurs to watch in the next 12 months?

  1. If you are a later stage company burning cash like crazy, and haven’t figured out how to turn a dollar into a dollar fifty or two, it is going to be tough. Seed and pre-seed stages are still getting done albeit may be taking a bit longer.

  2. If you are a consumer-focused startup, you really need to come up with a better go-to market than buying Facebook or Twitter ads because investors are seeing lots of money spent on ads, and it’s not as cost effective as it used to be.

  3. On the hiring side of things, over the last 6-12 months we saw salaries and stock compensation in tech skyrocketing. That’s beginning to stop. There are still lots of companies hiring, but Facebook and Twitter, who had been fueling a little bit of this frenzy, have both paused. It may be a good time to be hiring. We’re going to be seeing later-stage startups doing layoffs, which will introduce new people into the market.

What are your favorite resources / networking events local to Boston?

I follow a lot of founders on Twitter, some of them are local. I’m also plugged into Built in Boston and participated in a few Startup Boston Week events. There are some venture firms that get groups of founders for dinners, and I participate in those. I always look for ways to help other founders with connections and technical problems. I’ve been making mistakes professionally for over 20 years and I know where a lot of dragons are! I’ve paid close attention to Fintech Sandbox but I kind of lost track since COVID. Then there are a few communities that are just getting off the ground, like Mass Fintech Hub.

Come mingle with the startup community!

We hope you enjoyed this interview with this innovator! We’ll have more coming your way soon. In the meantime, don’t miss out on your opportunity to network with the startup community. Grab your free ticket for Startup Boston Week 2022 today!


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