Why 5 Chicago serial entrepreneurs keep coming back for more

by Andreas Rekdal
February 23, 2017

In speaking with Chicago's most successful tech entrepreneurs, one of the most common themes that often comes up is how hard the startup life can be. In fact, more than one founder has told us that they never would have started their company if they had known what it would entail.

But some founders still come back for a second, third or tenth go-round, knowing fully well what they're getting themselves into. We spoke with five serial entrepreneurs about what drives them to keep starting new companies and the hard lessons they learned along the way.


By providing employers with the tools they need to engage more deeply with their employees, HighGround helps companies hold onto their best people for longer. For founder and CEO Vip Sandhir, that mission meshes well with the most important lessons he learned founding Fooda and The BusBank.

What drove you to start your next company after going through the process the first time?

Though starting a company is painful, it was the challenge that drove me to start another one in 2012 with HighGround. No one believes you can do it. There is high excitement when you have a new idea, but also lots of ambiguity and uncertainty.

Most entrepreneurs start a second business for different reasons than their first venture. I’ve personally started businesses in a variety of different industries and I’m always seeking out good companies to build. At the end of the day, I’m driven by the simple challenge of building a great company.

What is the hardest lesson you’ve learned throughout your career as an entrepreneur?

Pick a good partner. You need to know and trust that your business partner is invested in the company for the right reasons. The same goes for your team. You need to hire the right people for the right mission. If you’ve ever hired the wrong team at the start of new business venture, then you know how hard it is to recover. However, finding a solid first crew and figuring out how to attract that talent is difficult. When recruiting, I’ve learned you can’t base hiring decisions on fancy resumes or company logos. I believe the startup gene is tied to the doing gene, and you should look for talent that embodies that attitude.

Lastly, I’ve realized that just because you’ve had a successful company before, that doesn’t mean you can afford to step away and focus less on managing and overseeing your team. Entrepreneurs need to find that balance of managing and overseeing staff but also still giving them freedom to do what they want.

How does that lesson help you in running HighGround?

I’m obviously biased, but I think I’ve hired the best team in Chicago of any of the startups. And it’s made my experience starting HighGround so much easier. I’ve also been fortunate to have the same investors and business partners in multiple companies.

Running HighGround, I’ve realized that it’s imperative to have a clear mission, vision and values for your business and to make sure you live up to them. Setting the foundational culture and values at HighGround has allowed us to be more purposeful from the start, and direct our hiring strategy. Still, starting a business is always a little trial and error until you get to the right formula.

Eved helps companies put on better events by streamlining procurement processes and reducing administrative overhead. Founder Talia Mashiach, who is also the co-founder of Access Chicago and a board member at the Chicagoland Entrepreneurial Center, said the thrill of building something from scratch is what made her step back into the fray.

We often hear about how hard it is to start a company. What drove you to do it, and to go through it again after the first time?

I don’t think I ever thought when I was younger that I was going to be an entrepreneur — they didn’t really have classes or a focus like they do today that you thought of that. I loved business, went to business school and I had a family very young and wanted to be home and raise my children. I started a company because I wanted something more to do and wanted flexibility to be home with my kids. Then it just grew from there.

While it was really hard to start my last company, I loved the challenge and overcoming that challenge building something from nothing. I am a person who needs to keep growing and challenging myself. Eved was the next challenge for me.

What is the hardest lesson you’ve learned throughout your career as an entrepreneur?

Things take twice as long and are twice as hard as you thought. I have that in mind when I am doing future planning to be more realistic about how quickly we can get there.

What is the most valuable piece of advice you’ve received from someone else throughout your career?

Enjoy the journey!

One of Chicago’s most seasoned entrepreneurs, Troy Henikoff is best known for founding SurePayroll and co-founding Excelerate Labs (now Techstars Chicago). Henikoff said founding a company is always harder than expected, but he still can’t imagine having a nine-to-five job.

What drove you to step back into the startup life after founding your first company?

When I look back at SurePayroll, we were trying to do something different. Payroll, prior to 2000, was always done by people calling an operator while the operator at the other end was typing stuff into a mainframe computer. We had this idea that since people were paying their bills online, why shouldn’t they pay their employees online?

We didn’t know how hard it was going to be, because we had never been in the payroll business, and everyone we talked to told us all the ways we were going to mess up. They were right and we were right. It was really hard, and we made lots of mistakes, some of which were costly. But we totally changed the payroll industry.

The types of people who become entrepreneurs are optimistic by nature. A pessimist would never go and start a business — there are too many things that could go wrong. But because we are optimists, we tend to go into the next thing being optimistic, too.

What is the hardest lesson you’ve learned throughout your career as an entrepreneur?

It always takes longer, and it always costs more money. I know this because I’ve done it 10 times, so the last time I wrote a business plan, I said, ‘Ah, but I’m smart. I know it’s going to take longer and cost more, so I’m going to overbudget to hit it right this time.’ But it still cost more and took longer than I was expecting.

With SurePayroll, when we raised our first round in 2001, it was an $8 million Series A. I could not figure out how we would ever spend it. But what I thought would take three years took 11, so we had to go back and raise more money.

Second, there is nothing more important than acquiring and retaining customers. So many entrepreneurs think they understand a problem and they understand the technology, so they’re going to create a great tool and people will just want it. But you have to go out and sell your product.

How do those lessons help you today?

One of my goals in starting Excelerate Labs was to help companies not make all the mistakes that I made. Just last week I was in a board meeting for a company, and they were running out of capital — they only had a few months of runway. I jumped up and down and said ‘We’ve gotta fix this now!’

Within 24 hours, we had a plan to extend the runway from three months to nine months. Nine months is enough to get some traction and go do something. They may not be off the ground yet, but they’ve probably increased their chance of success threefold.


Co-founded by Brad Bialas and Jaeme Adams in 2010, SwervePay helps healthcare providers and auto shops communicate with customers and receive payments via text message. Adams founded his first company in 1993, and SwervePay marks his fourth venture as a founder. To him, the lessons he's learned were a great motivation to keep starting new companies.

When did you first know that you wanted to be an entrepreneur?

I always found ways to connect people in order to solve problems. The more I did this, the more I understood that businesses are built on relationships. Leveraging these relationships turned into monetary success, and I was hooked. I wanted to find problems to solve with technologies and relationships, and I never stopped from that point forward.  

What drove you to start a new company after going through the process the first time?

Success, achievement and seeing things through when they seem impossible is addictive. But most importantly, each time you do it, you can learn from your past mistakes to deliver a better outcome the next time. That thrill of doing the impossible can’t be taught, it is just born with you. And that is what I believe makes us entrepreneurs.

What is the hardest lesson you’ve learned throughout your career as an entrepreneur?

You can’t do it all — give people tasks and trust they can achieve them. It helped me learn to build highly functional teams that focus on building on strengths, not covering for weaknesses.

And what is the most valuable piece of advice you’ve received from someone else?

Ask open-ended questions and listen to what people say. We have a tendency to think about how we are going to reply and really never listen.


Co-founded by YCharts founder Shawn Carpenter, RepIQ helps sales organizations find and qualify prospects. Carpenter said the most important thing he’s learned over the course of his career is that building a good company is all about finding the right people — but his idea of who the right people are has evolved over the years.

What drives you to keep starting new companies?

This is my third one, and in each case I’ve seen a better future and felt compelled to try to fix it. I couldn’t think of a more interesting thing to do than to solve a problem that seems like it’s there and waiting for someone to do it. And having been through it a couple of times, getting the team assembled and tackling that problem once you’ve identified it is one of the most exciting things I’ve ever done.

What is the hardest-earned lesson you’ve learned?

It’s all about the people. Early on, I thought only smart people mattered, but you have to get smart people that you also trust a lot. That’s the biggest thing, and I don’t think I understood that early on in my career.

Good people understand their role within the company and what the company is trying to do, they know their strengths and other people’s strengths, and they know their weaknesses. If you can find those types of smart people, you’re way ahead of the game.

How has that lesson helped you in running RepIQ now?

Instead of trying to hire Michael Jordan, I’m trying to hire the team that can do the best overall. We’ve tried to get really strong team players who are great individual contributors, but see their role in the bigger picture of the company. Even in selecting my co-founder, I tried to find someone who understood how important the team is, and how important it is to get the whole team working together. And that becomes even more valuable as you scale the company up.

What is the most helpful piece of advice that you received early on in your career?

One of my investors at my last company told me to focus on the problem, not the product. That’s something we focus on heavily at RepIQ. We’re really enamored by thinking about what problems we’re trying to solve, not about the features in our product or the cool things we can build.


Images via listed companies. Some answers have been edited for length and clarity.

What's your startup's story? Let us know with a tip or a tweet @BuiltInChicago

Jobs from companies in this blog5 open jobs
All Jobs
Project Mgmt

Chicago startup guides

Best Companies to Work for in Chicago
Inside the Best Software Engineer Jobs in Chicago
Tour the Coolest Offices in Chicago Tech
Inside the Best Sales Jobs in Chicago
Your Guide to the Best Perks at Chicago Tech Companies
Your Guide to Healthtech in Chicago
Inside the Best Data Science & Data Analyst Jobs in Chicago
Inside the Best Marketing Jobs in Chicago