This week marks the fifth anniversary of our exit to Aderant/Roper Technologies (NASDAQ: ROP)—one of the most significant milestones a founder can experience. While a “meaningful” liquidity event isn’t the only measure of success, it undeniably represents a well-deserved financial reward for years of relentless hard work, unwavering vision, and disciplined value creation.

Building and scaling a lasting enterprise is no small feat. Achieving a successful exit within just seven years, bootstrapped, is even more daunting, especially when half of all tech startups fail within their first five. Jason Lemkin of SaaStr recently highlighted a Carta report noting that the odds of a tech company scoring a favorable M&A outcome hover around just 1% to 1.5%.

I love Matt Turck's quote above, but I do not believe in miracles. Instead, I’d say that our exit was the result of a carefully orchestrated series of disciplined decisions, driven by a grand vision, bolstered by the right timing, and yes—some good luck. With this post, I want to share an overview of our journey leading to a second exit to a Fortune 500 company. Stay tuned for deeper dives into the details in future posts.

Time Is All You’ve Got

There’s no pun intended here—although our flagship product was a leading SaaS and mobile timekeeping solution for mid-size and large law firms. We set out to build a great company by optimizing every minute we had.

I feel genuine pain for founders who spend many years just trying to figure out product-market fit, their ideal customer profile, and effective sales motions, only to find out their hard-built product isn’t what customers want. Meanwhile, competitors enter the scene, and money burns faster than planned.

One of my many mantras was: “We’re going from A to B while making the fewest mistakes possible.” Redoing something is expensive—not just in terms of money, but also in lost market opportunities and team morale. It’s always hard, if not impossible, to fully recover from those setbacks. People often ask us, “How did you guys do it?”

Engineering Success from Day One

Having been through this before, we knew better the second time around. From the very beginning, we focused on engineering a company built for success. While there's no magic formula, we developed robust decision-making frameworks and internal playbooks that evolved with our growth.

Our metrics by exit time tell the story. Here’s what set us apart:

• 25%+ EBITDA

• 90% gross profit margins

• 110%+ net revenue retention

• 80% to 100% year-over-year revenue growth

• Zero debt

• Most importantly: stellar reputation and delighted customers

These numbers didn't happen by accident. We made deliberate choices:

1. Not all revenue is good revenue. We priced our subscription by firm size and user count, plus a setup fee. We never discounted recurring revenue—only setup fees—because our valuation was based on ARR. It made no sense to waste energy on revenue that wouldn’t enhance our valuation.

2. No customization or paid services. Though tempting, taking on custom work for extra cash would have hurt our valuation and distracted us from our core focus. We learned to say “no” and avoid customers who wouldn’t be profitable long-term.

3. Empowering teams with a “framework for success.” Leadership’s role was to equip each team member to excel—clear goals, proper incentives, solid training, and a strong culture. Ultimately, a company is only as strong as its people.

4. Revenue protection. Retention became as critical as earning new revenue. We implemented an early warning system (EWS) to spot at-risk accounts, take proactive measures, and quickly identify expansion opportunities.

5. Execution playbooks for growth and scale. Each function—operations, finance, talent, revenue, marketing, and development—had a living, breathing playbook. We constantly updated these as we grew, ensuring peak efficiency and focus.

6. Metrics obsession, financial discipline, and profitable growth. We never raised external capital, so it was our own money on the line. This perspective demanded a laser-focused approach to spending, growth, and profitability.

The Dating Game

About three years before our exit, we began receiving inbound interest from potential buyers—mostly private equity groups. Though we had zero intention of selling at that point, I started taking their calls. Think of it like “dating”: I wanted to understand the acquisition process, learn what buyers valued, and envision what a potential deal might look like. This early exploration was one of our smartest moves. It allowed us to learn the game and build relationships well before we were ready to sell.

I held weekly calls, diligently took notes, and stored everything in a “just in case” folder on my computer. Over time, I developed a clear sense of market valuations, buyer expectations, and the general M&A landscape. I also connected with investment bankers early on—again, just in case 😉.

Deciding to Sell

People often ask: Why did you sell? When is the best time? Was it too soon? And the classic: Could you let your baby go? (To be honest, that was a quick yes for me!)

Initially, we weren’t looking to sell. We wanted a growth-equity partner to help us scale faster and to gain some liquidity, taking a few chips off the table. Given our metrics—profitability, strong Rule of 40 performance, and founder ownership—private equity firms were very interested.

The year before our eventual sale, we received three unsolicited Letters of Intent (LOIs) that exceeded our valuation expectations. It suddenly got real. Still, we were on track for a stellar year and potentially even better results ahead, so we decided to pass. But questions lingered: What if this opportunity isn’t there next year? Could we do even better one or two years from now?

Deciding when to sell is deeply personal. In our case, we had no board or VC breathing down our necks. We owned the entire business. By Q3 of 2019, we knew it was time. The market was strong—2019 was the busiest M&A year since 2015. We hired an investment banker to help us run a proper, disciplined process.

This video below is a wonderful reflection by Jason Lemkin on the 20VC podcast: “I think I've given some pretty good advice over the years, especially on scaling revenue. But perhaps my worst advice has been on when to sell your startup. Here's what I got wrong:”

“If you get a good offer in bullish times, take it,” Bill Gurley.

Running an M&A Process

Working closely with our investment banker was instrumental. For about three intense months, I worked 14-hour days, speaking to our banker more than anyone else in my life. We prepared every detail—books, diligence materials, quality of earnings reports. Everything had to be perfect and transparent. Any mistakes could cost us in valuation, terms, or even scare off top-tier buyers.

Our banker reached out to around 100 potential acquirers—both financial and strategic. About 50% signed NDAs, and from there, we narrowed it down to 12 best bidders. This involved on-site presentations, long dinners, and nerve-wracking negotiations. Ultimately, we whittled the list down to three final offers: two from top private equity firms and one from a strategic buyer.

Time to Decide

We had 48 hours to choose from three amazing offers. The private equity buyers wanted to acquire 80% and partner for a future second exit. The strategic buyer offered an all-cash deal, a short consulting agreement to assist with the transition, and a five-year non-compete.

It was a tough call. The financial buyers dangled the promise of a bigger “second bite of the apple” down the road. But the strategic buyer—Roper Technologies (through Aderant)—offered alignment, transparency, and a clean, swift close before the holidays. Although not the highest bidder, Roper felt like the right partner, and I trusted their intentions.

30 Days to Close

Choosing Roper was, without question, the right decision. Their M&A and Aderant teams demonstrated integrity, transparency, and a sincere interest in closing on time. We were ready, too—clean books, zero technical debt, and disciplined operations. Every sacrifice we’d made, every ethical stance we’d taken, now paid off. We felt lucky and privileged, capping a chapter that only a few founders ever get to experience. We did it—again.

A New Dawn

After nearly two decades in the game, I was ready to pause, smell the roses, and try new things. But I had to face a new question: Without being a CEO running a legal tech company, who am I?

Exiting pushed me out of my comfort zone. I ventured into investing in minority founders and launched a venture capital fund, The Fund XX (now Everywhere XX), alongside incredible co-founders. It's fascinating, rewarding, and deeply meaningful work.

But the legal tech world still calls. The opportunities are more exciting than ever, and I'm ready to jump back in. Seriously. Stay tuned.

The journey from startup to successful exit is rare and challenging. It requires vision, discipline, timing, and perhaps a touch of serendipity. But most importantly, it demands unwavering dedication to building something of lasting value. This was our story - what will yours be?

Thank you for reading, and DM me if you are building something exciting or investing in legal tech.

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