According to Leigh Drogen, the co-founder and CEO of Estimize, there’s a big difference between working for or managing a traditional financial institution and a financial startup.

When you’re in charge of the former, “Every day you come in and know exactly what you need to do to build that firm,” Drogen, who was previously the founder and CIO of Surfview Capital, told StreetID. Drogen was also an early member of the team at StockTwits and led the development of the Chart.ly platform. “You have your strategy, you stick to it, you don’t stray from it. If you set expectations at a reasonable level — we told our clients we’re gonna make 12 percent a year no matter what.”

Drogen said that Surfview “crushed it” at 30 percent for the two years that he ran the company. “Setting expectations is very important,” he added. “But it’s very easy — if you set the expectations correctly — to meet them and exceed them.”

When you’re running or working for a startup, however, it’s completely different. “You have to come in every day and figure out how to make it work,” Drogen explained. “You have to make s*** happen. It is mentally exhausting to wake up every day and pry open doors and get people to do something that they’re not doing yet and build a new company from scratch. It’s not simple. It takes more mental energy than physical energy because every day you have to continually go at it because nobody else is going to help you. It’s just pure sweat that you’ve got to put in.”

Estimize is currently searching for a full-time designer who can also code in HTML and CSS, a system administrator who can also code in Ruby, and a back-end Ruby developer.

“We’ll eventually be hiring a couple of quants, six to nine months from now, because we’ll be building StarMine for our own platform,” said Drogen. “So we’ll be taking some quants and doing some interesting things with them.”

Drogen told StreetID that he is seeing a lot of finance and investment banking guys who want to get out of the larger financial institutions. “I’ve gotten a million resumes from asset management guys who want to move to startups,” he said. “They want to do more interesting things. I think they want a job that’s fulfilling, to actually build something. From my perspective, I found building Estimize and building StockTwits to be much more fulfilling, even though I loved being a trader.”

Working for a Startup

In working for a startup, one thing remains clear: you have to be able to believe in what the company is trying to achieve.

“Can you get [prospective hires] to buy into your vision of giving [them] some equity in place of $200,000 a year?” Drogen questioned. “It’s important to be able to do that, and that’s kind of what we look for.”

Further, Drogen said that Estimize tries to avoid the “halo effect” of “meeting the person, really liking them, and them not having the specific skill set that we need.”

“The second thing we are looking for is people who really blow us away at being good at anything,” he added. “It’s kind of like a professional sports draft. One strategy is that you draft for the position that you’re most in need of; the other strategy is to draft for the best athlete that’s on the board at the time. If we find one of those kinds of athletes that’s the best on the board and blows us away, we consider that as well and figure out what to do with them. They don’t come along often.”

Finally, Drogen wants prospective hires to be able to fit in with the company culture. “Do they really believe in what we’re trying to do?” he asks. “We are building something in a very specific niche. You really have to love behavioral finance and what we’re trying to accomplish here, because it is very niche and it may not carry over to getting poached to go to some other startup.”

Not a High-Pressure Culture

“It’s not a high-pressure culture, per se, and we do give unlimited paid time off,” said Drogen. “But it’s very much a culture of, you’re responsible for what you’re supposed to be responsible for. As long as you get your stuff done, that’s really all that matters. We expect a high level of execution — we don’t expect a high level of process.”

When it comes to running a startup, Drogen said that you need to have trust in your team “to take something and kind of deliver on the vision that I have and flesh out the details because I can’t be sitting in front of them and nobody wants to be handheld the whole way.”

“They want to be able be creative,” he said. “They want to do things their own way within our framework, and I think we give that kind of flexibility, which is something that they like because they feel like they’re driving the process as much as I am.”

Yes, Estimize Does Give Unlimited Paid Time Off

“We don’t count the number of days that you take off because we believe that’s kind of arbitrary,” said Drogen. “We pay very close attention to, if you’re going to take time off, make sure it’s during a time when it won’t affect anyone else. Make sure that your project, whatever it is you were working on, is pushed and complete and done and has no bugs, and that everybody knows where you are in the process, and that you’re not putting the team at a disadvantage at an important time or during the middle of a very important push.”

Drogen added that Estimize has somewhat of a “cyclical nature” because of the sector’s quarterly reporting system. “The month before earnings come out, nobody goes anywhere,” he said. “It’s all hands on deck. During those dead, four or five weeks in the middle, where there really are no earnings, that’s when everybody knows you can take some time off and refresh the batteries, just because we do have these very specific pushes every three months. And that wears people out. It’s very much an honor system type of thing. But I think it works very well. It’s great for morale.”

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