An $11M EBITDA services company was trapped by a deal made years earlier when the business was struggling. An early investor had negotiated a revenue share agreement that paid out half the company's free cash flow annually, $5M walking out the door every year. Worse, the investor held veto rights on any sale, and they were using that power to block acquisition offers. The investor was getting essentially a free dividend and had no incentive to let the founder exit. They kept pushing for acquisition valuations the founder would never hit, effectively trapping him in his own business.

The challenge was to remove the predatory investor without destroying the company's cash position or taking on crippling debt.

I advised the founder on a debt restructuring strategy using an existing, unused line of credit. We recommended buying out two years of payments to the investor upfront, eliminating both the revenue share agreement and the veto rights in one transaction. This gave the investor a lump sum exit while freeing the founder from long-term obligations.

The outcome: $5M added back to annual cash flow, veto rights eliminated, and the founder regained full control of his exit timeline and deal structure. The company is now positioned for acquisition without obstruction, and the founder can finally pursue offers on his own terms.

A cutting-edge AI company had built breakthrough technology with a robust patent portfolio, but they were weeks from shutting down. Poor sales execution meant too much time spent in pilots without pushing for contracts. High engineering development costs combined with an investor pulling out at the last minute left them nearly bankrupt. They had incredible IP but a terrible P&L, and traditional valuation methods made them look worthless.

The challenge was to find a valuation approach that reflected the true value of their technology rather than their failed go-to-market execution, and to identify the right type of buyer who could unlock that value.

I advised them on pursuing a strategic acquisition rather than trying to survive as a standalone business. We positioned the deal around their IP portfolio using the reverse royalty method. By identifying a strategic buyer who could deploy the patents across their existing business, we demonstrated that the acquirer could attribute over $300M in projected sales to the patent portfolio. This made the technology company's value based on what the IP could generate for the buyer, not what the struggling company had generated on its own.

Within months, they went from considering bankruptcy to fielding serious acquisition conversations. The company that would have been valued at pennies on traditional metrics became an attractive strategic acquisition because we repositioned the conversation around IP value, not operational performance.

A robotics distributor wanted to grow quickly, either to make a strategic acquisition or position themselves to be acquired. But their revenue was entirely founder-dependent. Every deal required the founder in the room, and there was no clear sales process the team could follow independently. Lead qualification was inconsistent, paperwork was manual and slow, and nobody had visibility into what was actually happening in the sales pipeline. This made the business unscalable and unacquirable.

The challenge was to create a repeatable, transparent sales operation that could function without the founder being the bottleneck in every deal.

I revamped their entire revenue operations from lead to closed deal. We rebuilt their HubSpot setup to automate paperwork and service agreements, eliminating manual bottlenecks. I worked with their outsourced marketing and SDR firms to tighten lead qualification, cutting through noise to double the rate of qualified leads entering the pipeline. Most importantly, I process-mapped the entire sales journey and visualized it for the team step-by-step, creating transparency and accountability across the organization. Now everyone understood what they were responsible for and could execute independently.

Within the first month, closed sales doubled. The company proved it could scale without the founder being in every deal, making it viable for either acquiring other businesses or being acquired themselves. Revenue was no longer trapped in the founder's calendar.

A public company's growth was being held hostage by its former founder. Despite no longer running the business, he owned over a third of the company's voting shares and was using that power to interfere with the CEO and board's strategic decisions. Every major decision required considering his objections, even when leadership knew he was wrong. The board was stuck: they couldn't ignore someone who controlled that much of the vote, but his meddling was paralyzing the company's ability to execute.

The challenge was to reduce the former founder's voting control to a level where leadership could make decisions without his interference, while doing so in a way that was legally sound and strategically smart.

I advised the company on a recapitalization strategy using treasury shares they already held. We developed a plan to issue those shares to the market in a way that would dilute the former founder's ownership percentage below the threshold where he could block decisions. This would allow the board's quorum and aligned leadership to outvote him on critical matters, effectively ending his ability to obstruct company strategy.

The company successfully executed the recapitalization. The former founder's voting power was reduced to a manageable level, and leadership regained control of strategic decision-making. The company could finally move forward without one shareholder holding the business hostage.

A boutique management consulting firm had deep operational expertise in their industry but was stuck trading time for money. They recognized that their insights into clients and market dynamics gave them unique deal-sourcing advantages. Their thesis: established market players could acquire cutting-edge technology companies and become differentiated platforms for private equity rollups. They wanted to transition from consultants to independent sponsors facilitating those deals, but didn't know how to make that structural shift or fund the transition.

The challenge was to transform their consulting practice into a credible independent sponsor platform while maintaining cash flow during the transition, then position themselves as serious acquirers capable of sourcing deals and attracting capital partners.

I advised them on a two-part strategy. First, we streamlined their consulting operations to maximize profitability with a skeleton team, creating the cash flow needed to fund their pivot. Then we worked on their independent sponsor structure, including how to position their operational expertise as their competitive advantage, develop their capital formation approach, and create a repeatable deal sourcing process within their industry vertical. We worked through the mechanics of how independent sponsors operate and how to articulate their value proposition to potential capital partners.

Within a year, they successfully raised capital and negotiated a merger agreement with board approval for a majority stake acquisition of a public company. They proved their model by executing multiple transactions and establishing themselves as credible operators in their space, transforming from fee-based consultants into equity-focused dealmakers.

I founded a case management software platform for criminal defense attorneys and raised $1M in pre-seed capital from a $500M venture capital fund on a SAFE note. At our peak, we were valued at $6M. It was my first startup and my first time raising capital. I did what a lot of first-time founders do: I fell in love with building the product and didn't focus enough on sales.

I had come from working in startups and thought I understood what it took to build a company. I didn't. I partnered with a venture studio that believed in the thesis but gave me guidance I ultimately disagreed with. More importantly, I realized the business wasn't viable in the form we were building it.

So I made a hard call: I returned the remaining capital to investors and wound down the company. But not because I was done with entrepreneurship. I realized I didn't fully understand the exit paths that would determine whether I'd built something valuable or just functional. I needed to learn M&A, deal structuring, and private equity—because those are the forces that actually control most outcomes for companies.

I went and learned how buyers evaluate businesses, how deals get structured, and what makes companies acquirable versus just operational. Now I bring that perspective to every client: I've been the founder trying to build something worth buying, I've made the mistakes, and I've learned what actually matters when the deal is on the table. I help founders avoid building businesses that work but can't be sold.