How Mario Damasceno Transforms Middle Market Investing with AI Magic

In this edition of the Wantrepreneur to Entrepreneur Spotlight, Mario Damasceno shares his journey from corporate success to founding MainSquare, a transformative platform for lower middle market investors. Inspired by a pivotal moment in private equity, Mario built a business model that leverages AI and a network of experts to enhance profitability and efficiency. His story is one of bold pivots and continuous innovation, as he navigates the complexities of entrepreneurship with a focus on long-term vision and personal fulfillment. Discover how Mario's unconventional strategies are reshaping the consulting space and empowering business owners.

Hi, Mario! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

MainSquare is a value creation and operating intelligence platform designed for lower middle market and search fund investors. We quickly diagnose critical value creation levers and deploy and network of skilled, highly technical experts to implement change. We directly impact short term profitability and operational efficiency on behalf of our clients.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

Last year, I had the 'lightbulb' moment while working in the private equity industry. I was fulfilling a role in the firm that I felt could easily be built and made more accessible for the lower middle market. So I went to work on building the business model, did some early market testing, had prospect interactions, and narrowed in on critical pain points. In January 2026, I refer to it as an 'itch I needed to scratch' and went all in building the business.

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

Building a very successful career in corporate America made me realize that the title and increases in salary provide short-term benefits, but don't amount to long term personal happiness. I came to the realization that those individuals who are most happy and most fulfilled are those who can integrate their personal and professional lives. And what better way than to be an owner and builder of a company you can call your own. 

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

I would be remiss not to mention the AI tools that exist now, as without these, I would be unable to build what I am building today. We leverage Claude and Base44 primarily with other ancillary tools for prospecting, deck creation, among other things. Our partner network continues to leverage the latest tech and tools to build faster, offering better, more competitive pricing for our clients.

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

We're on our pivot #10, probably approaching #11. The most impactful pivot was when we changed our ideal customer profile. I was pretty dead-set on who we were targeting was the right market, but very quickly realized there was a better market for us to begin talking to. And it has opened so many doors for us. 

What unconventional strategy did you employ that significantly impacted your business?

Our business model is very unconventional, as we are working to disrupt the 'generalist consulting space'. With the raise of AI and as technology becomes more and more advanced, we're leaning into the hypothesis that many smart people will be more willing to take the risk in developing new services for business owners. Our goal is to find them, showcase their service, and position them into businesses where they can have the most impact.

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

Treat everyday as a testing ground but always have a north star. When I decided to take the leap, I had thought I had this 12-month roadmap of a concrete plan, a weekly routine, etc. Quickly realized that every day you will test, iterate, pivot, and test again. Your business model is going to change 100 times before you narrow in on the thing that works. But maintain a long term vision of where you want to go. Otherwise you could end up going in circles and get lost in the day to day. Remember to pull yourself out of the weeds and stay big picture focused.

Want to dive deeper into Mario's work? Check out the links below!

• Connect with Mario Damasceno on LinkedIn: Mario Damasceno
• Follow MainSquare on LinkedIn: MainSquare
• Follow MainSquare on Instagram: @_mainsquare