Meet the crew

When I’m on the road doing my one-man-show speaking gigs, people always ask me about the team I work with back at the ranch.

Who are they, and what are they like?” They ask.

They’re all rockstars in their area of expertise” I say. “And they’re a ton of fun to be around“.

But here’s a little more about each of them and their role on the team. They all play in the sandbox with me in the BOSI Accelerator.

Steve Thompson is our resident human capital guru. He spent 25 years in senior human resource leadership with medium to large sized corporations. He was recruited to lead a startup that grew to over 540 million in revenues and went through an IPO. From 2000-2010, Steve was Principal at Sterling Partners (a Private Equity firm) that grow from $90 million to over $4 billion in assets during his tenure. His role at Sterling was to do diligence on incoming portfolio companies and build powerhouse management teams that could scale companies to massive revenues. In addition to being my business partner, he runs the human capital practice @ Dreihaus Private Equity. Third parties have told me he is in the top 2% of human capital experts in the country.

Tim Conway spent the first 15 years of his career in Marketing and PR for companies like Sears and McDonalds. He then transitioned into entrepreneurship to launch his own advisory firm. He then taught public speaking and marketing at DePaul University and now teaches entrepreneurship at Roosevelt University. Tim wears two major hats on our team. First, he heads up the development of any content and curriculum we create. He is our education czar. Second, he participates as a strategist when we’re working hands-on with a company to incubate or accelerate growth. His ideas come a mile-a-minute and he’s never shy of rolling up his sleeves and helping companies get important things done – especially in the areas of marketing and public relations.

Andy Parker is a serial entrepreneur like me. He’s built three technology companies from the ground up, raised tens of millions of dollars in funding, built huge sales teams, sold the likes of Microsoft on big-cash licensing deals. Andy plays two major roles on our team. First, he’s a master strategist and problem solver. I’ve sat with him through countless hours of strategy and never found him to not know what to do next. His brain is wired with so much Builder DNA, it’s not even funny. But more importantly, Andy is one of the few people I have ever found who rolls up his sleeves and goes to work in a startup or struggling company to create growth. Unlike most people who want to tell you what to do and then sit back and watch you do it, Andy shows you what needs to be done and then does it with you. That’s a priceless asset on a team like ours. Our portfolio companies are absolutely addicted to him.

Bob Rupczynski Bob is our digital marketing rockstar. But don’t take my word for it, know that top Facebook executives gave him that title. He was the brains behind Albert Culver’s competition crushing digital marketing rollout in the mid-2000’s. When TresSomme’ beat out Pantene in online marketing, that was Bob’s doing. He then joined Wrigley (yes, the brand we all love) and build their digital marketing footprint to one of the most dominant in the world. His Skittles Facebook page success was just featured in Forbes magazine. As busy as Bob is at Wrigley, I don’t call on him much, but when we’re incubating a startup or working with a SMB in our 18-month accelerator, Bob’s genius brain is always brought into the mix.

Jackie Camacho-Ruiz When you meet Jackie, you get the sense that she is always having a amazing day. Celebrated author, speaker and PR guru, Jackie runs her own marketing firm JJR Marketing. With a decade of marketing and public relations experience behind her, clients entrust Jackie with strategic planning, marketing planning and creative brainstorming. We ask her to play in the sandbox with all our portfolio companies when it is time to get big news coverage and leverage powerful media relationships to leapfrog the competition.


Trey Morris Trey is a sales and marketing machine…period. With over 100 million dollars in personal sales production over his career, he knows what he is doing. He comes from the advertising sales world but along the way has owned his own ad agency and full service marketing firm. He is also a restauranteur. He is co-owner of the best BBQ restaurant north of interstate 40 called Q-BBQ. If you’re ever in the Chicago area, we’ll be glad to meet you there for lunch! Trey engages when companies need a killer sales and marketing plan. He’s a no-nonsense, old-school sales and marketing guy. He’s not a digital marketer like Bob. He’s all about windshield time, building relationships and closing deals. So when a company’s business plan calls for people-driven sales and marketing, Trey’s our guy.

Satish Rao Satish is a financial model designing brainiac. I can’t say it any better than that. He is a Kellogg MBA who spent almost a decade with IBM Strategy and Change. He also works as a principal in a firm with world-renown professor and author Robert Wolcott. We bring Satish in when we’re working with a company that needs to raise a boatload of capital. Satish builds the financial model and participates in pitch training and investor deck prep sessions. I seldom trust anyone else to build a financial model for one of our portfolio companies. He’s one of the best I have ever worked with.


So there ya go! The team @ the ranch (and interestingly enough, the longest blog post I have ever created).