Today we’d like to introduce you to Drew Whiting.
Drew, can you briefly walk us through your story – how you started and how you got to where you are today.
Andrew Maratea and I started Whiting Maratea LLP in my kitchen in Lakeview on February 1, 2012. We were 26, fresh out of law school, and determined to carve our own career paths without being dependent on the whims of others or the economy. We had no idea what we were getting into, but had faith that if we worked hard and told everyone what we were doing, that things would work out.
We figured out how to handle evictions for landlords and early stage legal work for startups, and from there, we built our firm with the help and support of mentors, friends, and family. Business development came easier to us than the management of our business, but in the spring of 2013, after a few dates, we merged our firm into Axia Law, where with Alex Pappas and Patrick Wartan, we spent the next 4.5 years building a law firm that served entrepreneurs and investors in the real estate, venture capital and hospitality industries.
In the midst of growing our startup law practice, with Michael Shenouda from Honore Properties, we also started an angel investment syndicate called Breakpoint Ventures, which has invested over $500k in 7 early-stage venture deals since mid-2014, including some Chicago favorites, Home Chef, DRYV, KnowledgeHound and Provi, among others.
The Axia Law era was fun. We hired young, like-minded attorneys and staff who enjoyed working with creative and innovative clients who shared our entrepreneurial spirit. Walking into the office, the first two things you’d see were a Ms. Pacman machine and a kegerator, which was replenished regularly.
The Axia Law era was also difficult. In each instance when we had the opportunity to give ourselves raises, we opted to hire another team member to grow the firm. In addition, as our clients grew, so did their demand for a wider breadth and depth of legal services, which was out of reach for a firm built by a few guys barely in their 30s. We knew that growth would require a shake-up.
In late 2016, we began conversations to merge our practice with Stahl Cowen, a mid-sized firm down the street with the same energy, but with the gray hair and resources we needed to continue growing our practice with our existing client base. On the fifth anniversary of the founding of Whiting Maratea, the merger was complete, and we have continued to move forward with the same entrepreneurial compass, but a larger platform on which to grow.
Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Any entrepreneur who tells you the journey is smooth is lying to you. It is a never-ending, flow of highs and lows, with the highs higher and the lows lower than anyone is prepared to handle, sometimes separated by months, often only hours. Financial anxiety accompanies the stress and emotional drain of keeping a positive image to others, while struggling to sleep at night and get out of bed in the morning.
The last six years have taught me a lot about how to start and grow a business, but they’ve taught me more about myself. I’ve learned to use the energy from the highs to help power through the low points, and the despair of the low points, to be more appreciative of victories of any size. You can imagine that the benefit of this ability may impact other areas of my life.
The perspective gained through travel down a bumpy road also gives me the ability to provide better counsel to my entrepreneur clients. I’ve become a better listener, but more importantly, able to hear the contrast that often exists between the words of a voice, and a look in the eye. No better tool exists in my world than asking “How are you?” in a way that shows you both want to hear and care about the answer.
Stahl Cowen Crowley Addis; Breakpoint Ventures – what should we know? What do you guys do best? What sets you apart from the competition?
I head the Venture Capital Practice at Stahl Cowen, where we represent growth stage companies through seed and institutional stage capital raises, and provide general counsel to clients as they prepare for and put that capital to work. We also represent venture capital funds, family offices, and angel investors in the syndication of funds for investment, and diligence on investment deals.
My practice was built on being a central resource for introductions to key industry contacts, assistance with service provider selection and facilitation of meetings between those who seek capital and those who write checks.
The best introductions and testimonials I receive usually include some reference to my distinction as a “normal dude” who “gets it”. I’m still trying to figure out what that means exactly.
What moment in your career do you look back most fondly on?
The proudest moment was also the hardest.
In early 2017, as Axia Law was preparing for the merger with Stahl Cowen, office tension was justifiably heavy, and it felt like a funeral at times. In the final days, I broke down a few times, struggling with the decision we’d made and feeling awful about having pulled the rug out from under our team, the people who were now among my best friends and closest confidants.
On our last day in the Axia office, an associate told me to take a look around at what was happening, where people had landed, and to realize that all of that was a product of what we’d built. We had people going to some of the best firms and companies in the city, and a good contingent sticking together through the merger, and in the coming months, I would realize that the friendships we’d created at Axia would continue.
The proudest moment had nothing to do with the law, and everything to do with the relationships developed.
Contact Info:
- Address: Western & Armitage
- Website: http://www.stahlcowen.com/
- Phone: 3125159838
- Email: dwhiting@stahlcowen.com
- Instagram: @bauce86
- Facebook: https://www.facebook.com/andrewswhiting
- Twitter: @DrewWhiting

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