Why I Left a 10-Year Investment Banking Role to Buy a Small Business
After nearly a decade in investment banking, I left my role as a Vice President at KPMG Corporate Finance to pursue something entirely different: buying and operating one small business. Not a startup. Not another advisory role. An actual business with real cash flow, employees, and a customer base — something I could own, grow, and lead for the long haul. This is the heart of Elbert Street Capital, my independent effort to acquire and operate one great business through a model known as Entrepreneurship Through Acquisition (ETA).
From M&A Advisor to Owner-Operator:
In my investment banking career, I spent years advising small and medium-sized businesses (SMBs) on their strategic alternatives, including exits, acquisitions, and raising capital. I worked directly with founders and entrepreneurs across industries, helping them assess value, structure deals, build financial models, and ultimately, sell their companies.
I really enjoyed my company and especially my direct team, but after a while I realized I wanted something different. I didn’t want to keep working from deal to deal, advising from the sidelines. I wanted to step into the driver’s seat: to lead one business, build a great team, and get into the weeds of the operations, systems, and decisions that make companies successful in the first place.
So I began to research and prepare for what this path would entail.
Why Buy a Business Instead of Building One?
Many people chase the startup dream. I respect that. But I didn’t want to start from scratch, particularly given my experience.
Instead, I saw an opportunity to acquire a stable, cash-flowing business, bring my experience to the table, and invest in growing something that already works. With tools like SBA loans, seller financing, and thoughtful deal structures, this path (sometimes called a self-funded search) is more accessible than most people realize. But that doesn’t mean it is easy.
Through Elbert Street Capital, I’m searching for one business to buy and operate for the long term. You can view my acquisition criteria here.
Helping Other Business Owners Along the Way:
During my search, I’ve come across countless business owners who are open to selling or are already in the process, but their internal financial systems are disorganized, reporting is inconsistent, and they’re simply not ready. This doesn’t take away from the services their brokers and CPAs provide, but they need someone who can step in and help build internal financial structure well ahead of time: clean up QuickBooks, capture the right data, streamline reporting, implement better financial systems, and produce the kind of strategic analysis that actually drives valuation.
By putting these pieces in place well before a sale, owners can operate more confidently in the near term and command a stronger price when they’re ready to exit.
So while I continue to search, I’ve started helping in another way: offering fractional CFO services and short-term financial support to small business owners who need help organizing their numbers, understanding cash flow, or preparing for a future sale — even if I’m not the buyer.
If you're interested in that kind of help, you can learn more about my fractional finance services here.
What This Blog Will Cover:
This blog is a reflection my journey to buy and operate a small business as well as expertise from 10 years investment banking. I'll share:
Lessons from real deal flow and diligence
Tips on financial modeling, valuation, and deal structure
Insights into what buyers look for
Advice for owners thinking about selling in the next 1–3 years
Occasional posts on operations, mindset, and life after corporate
Whether you’re a business owner, advisor, or just curious about the ETA world, I hope this gives you a helpful, transparent look at how this process actually works.
Cheers, Rob