Leadership Lab

Leadership Q&A with Dave Balter, Founder and CEO, Mylestone

Leadership Q&A is a monthly series that shares insight from leaders within Boston's startup community. This month, we spoke to co-founder Dave Balter, Mylestone’s, an early-stage venture backed startup, Founder and Chief Executive Officer.

Balter, a serial entrepreneur, founded Mylestoned in 2016 and previously led the Transactions (M&A and Partnerships) Team at Pluralsight, via the acquisition of Smarterer, a venture backed skills assessment startup he co-founded in 2010 and led as CEO since 2013.

INTELLIGENT.LY: What was your first job?

Dave: My first actual job was mowing lawns for a small landscape company. The owner actually stiffed me and never paid for my last month. I was so mad about it. About 10 years later, I saw him in a tie walking to work, looking totally depressed. Somehow I felt vindicated. Karma is a bitch.

My first corporate job post college was accounting for Mercer Consulting. I used to walk around the office getting hours from all of the accountants, many of whom were single and cute. My boss eventually told me I was distracting everyone, and I noted that I was able to finish the job in half the time allocated. Somewhere in there, this was probably a lesson that corporate life wasn’t for me.

INTELLIGENT.LY: Share some of your hidden talents?

Dave: Who ever said I was talented?

INTELLIGENT.LY: What is the best leadership advice you ever received?

Dave: “That’s Impossible” — as we went to launch BzzAgent, we heard this over and over. This was the best and worst advice ever. The worst because, well, because in the end, anything is possible. The best because the art of starting companies requires you to believe the impossible is possible. Now when I hear this, it only fuels the fire to try to figure it out.

INTELLIGENT.LY: What’s the most essential function of your job as a leader?

Dave: Leadership is all about setting the tone of the business. That’s comprised of a few things:

  1. Hiring the right talent that can accomplish what you’re setting out to do.
  2. Clarifying Mission/Vision/Values, especially as the business evolves
  3. Setting the pace and directing the focus to the things that are the highest priority.

More than anything it requires continued, persistent, rigorous attention to the people and direction of the company at all times. If you set that right, any business can become successful.

INTELLIGENT.LY: This year you founded your 7th company, what are the key differences in your approach now versus your first startup?

Dave: Well one thing that isn’t different is a huge naivete about what it is we’re doing, which I think can be a huge asset. When we started in the death industry, we had no idea how the industry was constructed or the paradigms that were considered sacred cows. Sometimes non knowing enables you to become entirely creative to the solution.

INTELLIGENT.LY: If you could talk to the Dave from 10 years ago, what advice would you give yourself?

Dave: Probably to take it down a notch. Not in pace or courage, but in approach to those who didn’t quite see eye to eye with where we were headed. Sometimes you have to let people come along for the journey in their own way on their own time. A decade ago I might have been much more direct in calling people out who “didn’t get it”; now I might just move on to focus on those who do.

INTELLIGENT.LY: Talk to us about the importance of mentors and coaches in your professional life. How did these relationships begin?

Dave: I rarely sought out mentors or coaches, they just generally evolved, which is really important — it’s one of those things I think you can’t force. My first mentor was John LaPann at Federal Street Advisors, where I worked during Summers in college — but it was only after working together for a while that we understood how his talents could augment my natural state. Shikhar Ghosh became an investor in BzzAgent and over time he’s become the guy I turn to first when I’m truly stuck; that took years of learning and trust together.

The key is to work hard to foster great relationships with people you can learn from — mentorship and coaching is a natural outcome from that.

INTELLIGENT.LY: What advice would you give to first time managers?

Dave: Trust who you are and don’t get over-advised. You win from your core and need to focus on what you have that’s special to get to the outcome you want. Everyone has a super power, what’s yours?