We were lucky to catch up with Reuben Levinsohn recently and have shared our conversation below.

Hi Reuben, thanks for joining us today. What’s the backstory behind how you came up with the idea for your business?

After founding and exiting several businesses, I discovered my true passion: working with early-stage, innovative founders through our venture studio and advisory firm. Together, we help turn big ideas into market-ready solutions, supporting and funding startups from their earliest spark of ideation all the way to a successful exit.

It all started two summers ago (during Covid) on a beautiful, sunny day. A couple of co-founders were scheduled to pitch their startup at my office, but I had a different idea. I asked if they’d mind doing their pitch in my plane instead—after all, I wanted to go flying. That flight turned into something far more meaningful than a pitch. The conversation was authentic, real, and personal, and by the time we landed, they were buzzing with excitement. They suggested I do this more often—and even capture it all on camera.

Fast forward to today, and Flying with Founders is more than just an idea—it’s my weekly reality. I merge my passion for supporting founders with my love of aviation, sharing the skies with entrepreneurs who are shaping the future.

But Flying with Founders is not just a podcast; it’s a movement. We’re redefining what venture support looks like, offering financial literacy workshops, exit planning programs, and retreats focused on personal and leadership growth. Unlike traditional venture capital, we believe the real “hockey stick” growth should happen with the founders themselves—not just their businesses. Because when founders thrive, their ventures soar.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m an entrepreneur at heart, but my journey didn’t start with that title—it evolved over years of building and exiting several businesses. Along the way, I realized my passion wasn’t just about scaling companies; it was about empowering founders. I wanted to do more than help businesses succeed; I wanted to help the people behind them grow, lead, and leave their mark. That’s when I shifted my focus to working with early-stage founders through our venture studio, venture fund, and financial advising firm.

At Washington Avenue Advisors, we don’t just fund startups—we guide them. We take founders from ideation through exit, providing support that goes beyond just the numbers. Whether it’s strategy, leadership development, or financial literacy, we believe in building the founder alongside the business. Through our Valuation Acceleration and Exit Readiness program, we prepare companies and their leaders to make smart decisions that drive long-term success. What sets us apart is our belief that personal growth fuels business growth, and that philosophy is woven into everything we do.

Flying with Founders is an extension of that mission. What started as a spontaneous pitch in my plane has grown into a platform where I combine my love of aviation with my commitment to entrepreneurship. Each week, I take founders flying, sharing their stories and diving deep into what makes them tick.

What I’m most proud of is seeing the transformation in the people I work with. When a founder steps into their leadership potential, it changes everything—their business, their life, and even the legacy they leave behind. That’s what drives me every day – SLEA, Servant Leadership through Entrepreneurship and Adventure!

If there’s one thing I’d want people to know about my work, it’s this: we’re here to make the journey of entrepreneurship as transformative as the destination. Whether you’re a founder looking to scale your business, a leader seeking clarity, or someone with a big dream ready to take flight, we’re here to help you make it happen. And we’ll do it in a way that makes you not only a better entrepreneur but a stronger, more fulfilled version of yourself.

Can you talk to us about your experience with selling businesses?

I started my first company at 21 yrs old while attending Michigan State University – a residential painting company. I worked with a franchise system to bring tech into this sleepy industry, creating a better experience for the customers and the painters. I built this up to become the largest (non-union) painting company in Michigan at the time (late 90’s – early 2000’s) and then decided I wanted to sell it and move onto something else – a reinvention of sorts that most entrepreneurs go through at least a couple times.

After a frustrating and long process of selling and then transitioning out of my business the buyer failed to keep the company running smoothly and eventually ‘gave’ it back to me in a poor state. I had to jump back in and clean things up, get it running well again, and re-sell it. It was rough but I made out ok! I learned so many key lessons from this experience and I wanted to share it with other business owners.

Fast forward to today – my partners and I at Washington Avenue Advisors (Lansing, MI) provide exit-readiness and valuation services as well as financial planning for many driven entrepreneurs. We are passionate about helping entrepreneurs grow the value of their greatest asset – their business, and eventually see the fruits of their labor with a healthy M&A or Succession planning transaction.

Can you tell us the story behind how you met your business partner?

Throughout my career, I’ve had the privilege of building and running several companies, and along the way, I’ve had the opportunity to work with some truly incredible people. I’ve hired, collaborated with, and unfortunately, sometimes lost amazing talent due to market conditions, shifting interests, or life’s unpredictable twists. By the time I turned 35, I realized something important: the cycle of finding, investing in, and losing great people was unsustainable—not just for my businesses but for me personally.

That’s when I made a pivotal decision: instead of treating my best people as employees, I would invite them to become my partners. This shift completely transformed how I approach leadership and collaboration. Today, I’m proud to be a founding partner in five businesses alongside 12 extraordinary partners, each bringing their own unique superpowers and skill sets to the table.

What makes this model so powerful is that our strengths don’t just add up—they multiply. When you align with the right people, 1+1 isn’t just 2; it becomes exponential. That synergy has been the driving force behind our collective success, and I consider it one of the most rewarding aspects of my journey as an entrepreneur. Working with these exceptional partners has not only enhanced our businesses but also deepened my belief in the transformative power of collaboration.

Contact Info:

• Website: https://Www.waadvisors.com
• Instagram: https://www.instagram.com/flyingwithfounders/profilecard/?igsh=Yjdld3NranA5bnk0
• Facebook: https://www.facebook.com/profile.php?id=100083110140857
• Linkedin: https://www.linkedin.com/company/flying-w-founders/
• Other: https://www.linkedin.com/company/washington-avenue-advisors/

The information presented does not involve the rendering of personalized consulting, investment, legal, financial, or solicitation. Investment advisory services offered through Washington Avenue Advisors, LLC (“WAA”), an SEC Registered Investment Advisor.