If you can dream - and not make dreams your master;
If you can think - and not make thoughts your aim;
If you can meet with Triumph and Disaster
And treat those two imposters just the same;
If - (“Brother Square-Toes” - Rewards and Fairies) - Rudyard Kipling
When Brad, the co-founder, called out of the blue, I braced myself. It had been almost a year since we last spoke, and the business he had built seemed to be in its final days. I expected to hear that they were shutting it down, another casualty of a relentless market and post-pandemic upheavals.
Over eight grueling years, Brad and Monica refused to give up. Despite threadbare finances, ruthless competitors, and pandemic-induced challenges, they persevered. Their dream was to prove the need for a challenger in a market ruled by a Goliath
Yet they had kept going - experimenting, iterating, searching for a way to prove out their business or perhaps better phrased, prove the need for a #2 player in a market that had been proven out but also dominated by one player.
They were trying to be the Lyft to Uber, the Android to iOS, the Twitter to Facebook. At every twist and turn they had run into headwinds that arose as a result of their resource constraints, their lack of scale, the fear of upsetting the incumbent, on whom so many industry participants were now dependent, despite the incumbent's predatory tactics.
I had expected them to quit years before - I wouldn't have been surprised or disappointed. They had surpassed our expectations in terms of their company’s lifespan - they had somehow managed to keep securing small checks and minor partnerships to keep the lights on and the flicker of the dream alive. So on this September afternoon, the unexpected call from Brad had all the markings of the final whistle.
As I pulled my mind back from the flashes of the business’ life that were zooming across my mind, Brad’s next sentence started out as I was expecting - “So I wanted to update you about the business….
…..We’ve secured a buyer for the whole company. It's an all cash-transaction which closes in 8 weeks. You’re going to get all your money back. It’s not what we had hoped for, nor what we had pitched you 7 years ago, but I hope you are ok with the outcome?”
I was stunned. Lost for words. - this wasn't just unexpected, it was MIRACULOUS!
I couldn't believe my ears. I asked him to repeat what he had just said and this time I could tell he was smiling a little - I was grinning like a Cheshire cat! I became effusive in my praise for him, for his resilience and persistence. The honor and grace he was showing in delivering this amazing news in such an apologetic way.
As an early-stage investor for nearly a decade, I’d come to terms with the reality that most ventures don’t succeed. Yet here was Brad, embodying resilience and integrity, delivering not just closure but a win. It was a poignant reminder that perseverance often outlasts expectations.
Brad & Monica’s business had experienced so much hardship and ultimately we had known for a while that it would never reach the scale of the Goliath-style incumbent it had tried for so long to fell with a sling and a rock. As such we had written the investment off - marked it as zero in our investment balance sheet.
So to receive the news that we would be getting our whole investment back, in cash, in 8 weeks, was nothing short of a miracle. An add-back!
This was a WIN. Or at least it felt like a HUGE WIN.
When I told my two investing partners they were similarly thrilled - the company had snatched victory from the jaws of defeat.
On top of this, and honestly more important to me at this point, was that both the founders were happy-ish with the outcome. Per her aims, Monica was going to work for the acquirer full time and Brad would be a consultant for a year, which suited his ambitions to build something new. The best part is they would both get back all the personal money they had invested.
As we wrapped up the call, Brad lamented that he would never get the 8 years back that he had poured into the dream of building this business. We mused on the fact that start-ups are hard and the path to success isn't always bookended with a huge outcome - often it's the experiences and lessons that are the true rewards.
Shortly after we had made our first investment in Brad and Monica’s company, Brad introduced me to Lance, a good friend of his from high school, who had just dropped out of his MBA program at Harvard to start building a digital media business.
I met Lance in person for the first time in the lobby of a downtown hotel. Tall, confident and bearing a vague resemblance to Ashton Kutcher, he was quick to share with me the excitement for what he was planning to build and the magnitude of the impact he thought it could have.
At that point all he had to share with me was a keynote presentation on his Macbook, but he painted a vision of social feeds filled with video, brands clamoring for content to post and the massive disruption that was coming for content creation of all kinds. He was a visionary and (in hindsight) his prediction was spot on.
Better still, he believed he had the perfect solution for this new, video-content driven world and he had already secured a small amount of investment, as well as some office space, from a production company founded and led by a legendary Saturday Night Live creator.
Lance and I agreed to stay in touch. A few months later and after getting to know Lance better, attempting to verify his vision and the size of the opportunity, Nucleus made the first of what would be a number of investments in this fledgling business.
Both at the time and in hindsight, Lance’s drive and vision made him one of the most dynamic founders I’ve worked with. Together, we tackled challenges in leadership, partnerships, and scaling - my first foray into coaching a founder executive and understanding the rollercoaster ride of building a business from scratch.
After passing through a high-profile digital accelerator, the business had reached escape velocity and investors started asking how big this business could actually be.
However, as 2021 was coming to a close, Lance had another visionary prediction - that private market valuations were not sustainable and that it would be better to sell the company while we could.
The buyer was a high profile, privately held, media company poised for an IPO and with the backing of the world’s largest asset manager and Hollywood royalty.
The headlines of the deal seemed super exciting - a 9-figure exit valuation for a company we had invested in as an idea on a digital-napkin and much like our first investment outcome, we were getting shares in a hot technology company slated to go public.
However the devil was in the details.
Details that the investor group never truly had enough time to understand as the buyer managed to create a sense of urgency tied to the approaching year-end and the necessity to file an S1 form with the SEC as part of their planned IPO.
There were so many moving parts to the actual transaction, backed up by an army of lawyers on the buyer's side, it was basically impossible for the investor base of the company, composed of almost exclusively private individuals, to truly comprehend all the nuances of the agreement.
The deal closed on December 30th 2022 - the last business day of the year. What should have felt like a huge win felt strangely disappointing.
Over the next year, the deal unraveled. Delayed cash payouts, canceled IPO plans, and plummeting valuations left us with far less than expected. What once felt like a win was beginning to feel more like a sobering loss.
Despite making money, the experience was filled with frustration and disappointment and never met our expectations.
The parallel tracks of our investments in Brad and Lance’s businesses were uncanny. Tracks that had taken dramatically different paths over a similar time period had arrived at their outcomes at similar times.
For Brad and Monica, the bittersweet reality of letting go of an eight-year dream was tempered by a sense of achievement. For Lance, a high-profile exit turned into frustration as unforeseen setbacks unfolded.
The journeys of Brad, Monica, and Lance illustrate that success in entrepreneurship is complex and multifaceted. While Brad and Monica's exit seemed like a miraculous win after years of struggle, Lance's high-profile deal left him frustrated and disappointed.
These contrasting outcomes highlight that our expectations shape how we perceive success and failure. Brad and Monica adjusted their definition of success over time, finding satisfaction in perseverance and personal growth even without building a billion-dollar business. Lance, on the other hand, faced disillusionment when his grand exit fell short.
As an investor and coach, I've learned that resilience, adaptability, and a willingness to reframe success are essential. The path of entrepreneurship is rarely linear—it's filled with unexpected twists, triumphs, and setbacks.
Ultimately, success is not just about the destination, but also the lessons learned and the person you become along the journey. Brad, Monica, and Lance each emerged from their experiences stronger, wiser, and more resilient. That, in itself, is a profound victory.
In so many aspects of business and life, sometimes a modest win can feel monumental, while a splashy exit can ring hollow. The key is to stay focused on the deeper meaning and growth that come from pouring your heart into a vision, no matter the outcome.
What defines success for you? In your work? With your partner? In your family? Has this changed recently? Why…..?
