If only we could go back and change things 😔

“It's not the path for everybody, but I think for some people, it's the only path.”

While the road to entrepreneurship is never easy, for some people, the journey is full of a few more twists and turns than they may have anticipated.

Driven by the desire to fulfill a dream or see a great idea through to the end, the bumps along the way don’t make them give up… They push them to keep going.

That’s exactly what happened to James Marciano, Founder of Tuck Advisors, nearly three decades ago.

Through founding multiple businesses, learning some big lessons, and picking himself up to try something bigger and better, James finally found himself in a place that feels fulfilling and meaningful.

But getting there definitely wasn’t a smooth adventure.

Entrepreneurship just seemed like the right choice

“On both my mom's side and my dad's side, my forefathers had all been entrepreneurs for basically as many generations as you can count. Literally nobody in my family had ever had a job outside of a family business.”

Growing up on the family farm in rural New Jersey, James was aware of what went into entrepreneurship, albeit on a smaller scale.

By the time we went to school, first, a private prep school in Princeton and later, Harvard University, he had a slight feeling that he didn’t fit in.

His peers all came from white-collar families, doctors, lawyers, etc., while he grew up with the mindset that you worked hard to make it.

When graduation hit and it was time to figure out what to do, he hit a wall.

Without any mentors or friends to talk to about business in the “real world,” he ended up going back to the farm, struggling to figure out what he’d do with his life.

He applied to countless consulting firms, spent endless hours mulling over his future, and even considered enrolling in the military.

That’s when he got a call from a firm in Los Angeles he had applied to.

Accepting the job, he spent a couple years consulting, during which he felt a growing frustration. He liked helping solve people’s problems but noticed, nothing was really being implemented.

This was during the dawn of the internet (remember the AOL floppy disks?), and James had a feeling there was something else better for him out there.

He knew it was time for a change.

Navigating a new world in real time

“I really regret how I handled the situation when we sold the company… I was a young founder. I should have spent money on an attorney and asked, ‘What should I do about the angel investors?’ And frankly, I just kind of ignored them because I was afraid we'd get sued or something. It was a whole mess. There's so many things I wish I had done differently with that first one.”

Selling everything he owned, he moved onto his brother’s floor in NYC, and decided he’d build an internet company called TheSquare, one of the first social media networks.

As he went through the steps to get his business up and running, he found he wasn’t experiencing emotions like fear so much. Instead, it was a lot of frustration.

He was navigating a new world as it was being built up around him. For example, registering a domain was done by faxing in paperwork and took 6 weeks.

He learned about 55 Broad Street in Manhattan’s financial district and invested in an office there, hoping to be surrounded by others in the same boat as himself.

But he didn’t have a solid plan. There was no one who had done these things before them. They were all figuring it out in real time.

James even had to convince a woman at the New York Times to create a new section in the classified titled “Internet” so he could put out a job ad.

“And then from there, you just start swinging. It's kind of like you’re blind in a dark room, and you just start swinging, hoping to hit something. That was the strategy, basically.”

Then, as things were taking off, he successfully raised millions in Series A funds… Just a couple days before the market crashed.

Even with money in the bank and a team of people, everything was crashing around them and he decided to sell the company.

(He was even featured in the documentary Silicon Alley Stories, highlighting “their incredible rise and fall through the dot com boom of the late 1990s.”)

Looking back, it’s one of the moments he wishes he could go back and navigate in so many different ways.

“Eventually, we wound up selling that company to one of our angel investors, and there's a lot of things I would have taken back. At that time, I probably would have just sat on that money, and I wouldn't have done anything for 6 to 12 months… We could have bought dozens of companies, essentially, for nothing.”

Unfortunately, there was nothing he could do after that, except learn from his mistakes and use them to inform future decisions.

Long days and a growing desire to keep going

“I think my mind was just popping with so many ideas. It was like, ‘What can I do next? What do I have bandwidth to focus on?’ I've always enjoyed working on multiple things together, because ideas from each cross over.”

While building TheSquare, he started a second company in 1997 called Refer-it, the first directory of affiliate/associate programs for e-commerce companies.

He wasn’t quite sure of the idea and essentially decided with a flip of a coin… A decision that ended up being fruitful.

Between the two businesses, he spent nearly every hour of the day, 7 days a week, working on figuring everything out.

Eventually, he ended up selling this one too… And experiencing another moment he wishes he could go back and change.

But this one was different. This led him to where he is now.

“I wound up negotiating the deal on my own, and I left millions of dollars on the table. That stuck with me, and that's why I have the company that I have today.”

After navigating yet another deal that could’ve gone better, many people would’ve thrown in the towel and commended themself on giving it an honest effort. But James wasn’t done.

Using mistakes to discover what really matters

“After my motorcycle accident, I really had to take time out for about a dozen years to recover my health. During that period of time, I was getting calls from people who were asking for help, ‘Can you help me raise capital? Are you interested in investing capital?’ So I transitioned to an angel investor role.”

When James took a step back and looked at everything he had been through, he realized he had some pretty valuable knowledge for those who were in his shoes decades earlier.

He had built companies, taken angel money and venture capital, had then become an angel investor and an LP in venture capital funds… He’s sat at every seat at the table.

Taking all his insights and lessons learned, he decided to build an M&A firm for founders to make sure they don't leave millions of dollars on the table the way he did.

Now, all the hard work of 25+ years finally started to pay off. He was able to work with people who felt aligned: mission-driven founders and companies that have a positive social impact.

“I love my job, I have the best job in the world. I get to talk to founders every day and hear their story. I have to remind myself daily that this is my choice, that I'm really blessed. I'm really grateful for this, and that I shouldn't complain about the hard work.”

The rewarding moments that make it all worth it

“You’ve got to work really hard and also have some form of luck, and you’ve got to be right. You’ve got to be right or willing to pivot to become right.”

Even when things don’t go smoothly, there’s always something that keeps entrepreneurs like James in it for the long run.

While many think entrepreneurship is risky, he believes it’s the opposite… That the risk comes in giving his career to someone else.

Being willing to take a bet on himself enables him to do what he really needs to do to find fulfillment in life.

He’s been able to work with people who truly believe in his mission and who have shared the journey alongside him.

He’s also been able to directly impact the lives of those who work with him, for example, when deals go well and income is steady, they’re able to buy their first house because of it.

From a humble beginning on a farm, being the first to go to college, and having survived some of the most trying times in his past, this whole journey has been one wild ride.

“I would say one of the most satisfying things is being able to have these lived experiences that I can share with these other people.”

Key takeaways from a long, winding road

It’s been decades of learning and growing for James, and in the end, he truly feels he’s come out on top. And no matter what he was working though over the years, these two things really stood out to him:

🌱 Be willing to make sacrifices

Especially at the beginning, sometimes time matters. That means missing out on things that hold meaning in your life. Are you willing to put aside friends and family at times?

🌱 Solo founding just doesn’t work

There’s so much to get done, more than you can possibly do yourself. People with complementary skills can help each other and the business grow in ways that you could never do alone. Even if you’re founding alone, there will always be people there to support you.

When’s the last time you audited your own wellness?

You get plenty of advice. What you rarely get is a pause. Each month, we’ll share a simple prompt to help you step out of execution mode and consider what “founding well” looks like in your world right now.

Your time tells a story... Not about how productive you were, but about what received your energy, attention, and care. As you reflect on the past week, notice what felt nourishing, what felt draining, and what your calendar might reveal about what you need more of right now.

Feel free to pull out old fashioned pen and paper, or create a new doc just for journaling, and spend a few focused moments thinking about the following:

• Looking back at your week, what felt draining, heavy, or more demanding than it needed to be?
• When did you feel most energized or engaged?
• Were there any moments of joy, rest, or play that stood out?
• What does the way you spent your time reveal about your current priorities?
• If next week could feel 10% more supportive, what would you make space for?

There’s no right or wrong answer. If nothing comes up, that’s okay too! Use this as space to notice what is real for you today. A few messy lines are enough.

If you're comfortable sharing your insights with us, let us know at foundingwell@vallelegal.com.