Interview with a Millionaire

Interview with a Millionaire

Michael Alter - posing for an interview with Forbes in 2015

For one of my classes (my favorite class, actually), New Venture Strategy with Professor Jim Schrager, my final assignment is to write a “Make Me a Million” paper, where I interview an entrepreneur who has made his or her idea into a business with an estimated net worth of at least one million dollars.  The objective is to gain a deep understanding of how this individual transformed the seed of a business idea into a successful enterprise.  What was the inspiration? What were the challenges and setbacks? What were the risks and how did they determine whether those risks were worth taking?

I took advantage of our Executive-in-Residence (EIR) program here at Booth and reached out to Michael Alter, former CEO of The Tie Bar. Michael is also cofounder and former CEO of SurePayroll; as well as an adjunct professor of entrepreneurship here at Booth.

We focused our conversation on his experience with SurePayroll, a SaaS technology company that is now a wholly owned subsidiary of Paychex ®.  Michael told me about the creative process he went through to build a product that fulfilled the unmet need for payroll services for small businesses. It was quite a roller coaster ride hiring a talented team of experts and renaissance men to get the business up and running. Not to mention the personal challenges of abandoning his partner trajectory at McKinsey in their service operations practice to pursue this path of uncertainty.  As someone without an entrepreneurial bone in her body, I was fascinated by Michael’s comfort with and ambiguity and ability to commit to a vision despite the uncertainty of the business.

One point which resonated from our conversation was Michael’s attitude towards risk.  He said that he never viewed leaving his partner track at McKinsey to co-found SurePayroll as a risk.  It was an exciting opportunity with a chance of failure just like any other career decision he had ever made.  His business school education coupled with years of sales experience at IBM and consulting at McKinsey had provided him with invaluable tools to help him make the business a success.  But it also gave him the confidence to know that he could always try something else or go back to either of his previous careers if he couldn’t make it a success.

And for someone like myself who has written off the idea of entrepreneurship because I have always categorized myself as risk-averse, this gave me some great perspective.  Being an entrepreneur isn’t about being a risk taker.  It is about making a decision to try something that has a chance of failure, like everything else, because the idea of succeeding excites you.  So while I still don’t think I’m going to start my own business any time soon, one day I can see myself doing exactly what Michael described- seizing an opportunity to pursue something that really excites me, knowing that my Booth education, network and experience will give me the best chance for success…even if it’s not a 100% chance!

In addition to getting unique perspective into Michael’s path to founding SurePayroll, this was yet another moment when I found myself pausing and reflecting on the doors Booth has opened for me.  A year ago, I would have had truly no idea who to interview!  But now, within 20 minutes of receiving the assignment, I came up with a list of 5 people I could reach out to that I personally knew.  And within 40 minutes, I had a list of 20 people that I knew of through my Booth network to whom I could reach out.

Booth has opened so many doors for me into worlds I never anticipated entering: brilliant academic research, Nobel prize winning theorems, the art and craft of a venture capital pitch, the legal infrastructure of business, and so much more.  Getting a glimpse into the domain of entrepreneurship was simply the latest addition to this list. And it was eye opening!

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