I Have No Idea What It Means to Be a Successful Entrepreneur

I have no idea what it means to be a successful entrepreneur.

That may sound like an odd thing to admit, particularly after a career that has been both entrepreneurial and, at times, successful — but not necessarily both at once.

For most of my professional life I've been launching businesses, initiatives, and programs that didn't exist before. Sometimes inside organizations, where "intrapreneur" is probably the more accurate term; sometimes alongside founders; and now, finally — or, perhaps more accurately, again — for myself.

I've built new business lines, new programs, and new initiatives, usually without much of a template and often without much support, whether in people or in capital. Creating something from nothing has always been the part of work that has energized me most.

Take, for instance:

• Football Partnerships: a B2B community for soccer industry professionals
• PlayBeautiful: a month-long brand and customer experience activation during the 2010 FIFA World Cup
• Upper 90 Soccer + Sport (Brooklyn): whose interior design and operations were inspired by PlayBeautiful
• UNICEF Enterprise: a social enterprise and digital engagement platform for corporate social giving
• BoxDroppers: a moving company
• RubyApps DevCamp (later RubyLaw Symposium): along with countless other programs, initiatives, and business lines launched at a software company that we later sold.

I've also had the privilege of leading sales and marketing for a startup that achieved a successful exit. I know what success looks like, and I know what it feels like to work inside an organization where momentum, structure, and a shared sense of purpose galvanize people toward greater heights.

When those elements are lacking, however, the opposite can occur. The perceived security of the traditional career — steady pay, health insurance, and interpersonal relationships — is neither guaranteed nor, in some cases, particularly fulfilling.

Entrepreneurship doesn't eliminate that uncertainty. It simply changes its source.

The beauty of being an entrepreneur is that none of those structures exist, and all of them do.

There is an incredible amount of freedom the entrepreneurial life. Every morning, I can decide how to spend my day, where to invest my time, which opportunities deserve my attention, whether today is a day for client work or building infrastructure, whether to buy another piece of software or continue making do with what I already have. In theory, no one tells me what my priorities should be.

I can pop by Ost for a coffee, check out a new development site on Broome Street, pop over to Sunday to Sunday for a nibble, do a bit of work, catch a midday World Cup match, and be ready on-time to scoop my kiddos from camp.

The reality, however, is that every one of those decisions has consequences. Unlike inside an organization, there is rarely anyone else to absorb them — or to tell me, "Hey, drop that. Do this."

If I decide to spend a week building a tool instead of generating pipeline, that's my decision. If I invest in the wrong software, the wrong marketing campaign, or simply spend too much time perfecting something that only needed to be good enough, there isn't another department quietly correcting course.

I lose money. I lose time. I lose momentum.

And momentum is extraordinarily difficult to recover once it's gone.

With familial responsibilities at both ends of my day, optimizing money, time, and momentum has become my best opportunity to gain traction and make meaningful progress. When I don't optimize, though, success seems to notch just a little farther out of reach.

Dear reader, I'm aware: None of this is particularly novel.

Most of the people I know professionally have experienced some version of these trade-offs. Some have spent decades inside organizations, steadily climbing corporate ladders. Others have built companies from scratch. Many have moved back and forth between those worlds, discovering that each comes with its own comforts and its own anxieties.

I arrived at my current venture — bridging real estate and entrepreneurship — later than I would have preferred, although in hindsight I recognize that timing as a privilege rather than a disadvantage. I wasn't forced into entrepreneurship because another door had closed; I chose it because the work I'd done previously had given me experience, confidence, and enough financial stability to take the risk. (It also doesn't hurt to have an extraordinary partner who has supported that decision while building an impressive career of her own.)

What that privilege doesn't provide is immunity from uncertainty.

If anything, it has made me more conscious of the psychological differences between building someone else's business and building my own.

Every morning I wake up genuinely excited by what I'm building. I also wake up knowing that every day I fail to create another opportunity in my pipeline is a decision whose financial consequences I won't fully appreciate for another three to six months.

That's a much longer feedback loop than exists within most traditional careers. If I accepted a role tomorrow, I'd receive my first paycheck in a fraction of that time. The work I do today as an entrepreneur may not produce revenue until I'm taking my scarves and winter accessories back out of storage.

I've found that delay surprisingly difficult to adapt to because it removes the immediate reinforcement that many of us unconsciously rely on. Instead, it forces me to trust that the work I'm doing today is the work my future business actually needs, even though I won't know whether I was right for months.

This realization has also forced me to confront something less comfortable about myself.

Left alone, I default to building.

I build because I enjoy it. I enjoy solving problems. I enjoy designing systems. I've written more than 250 articles. I've built AI tools (Budgetizer, NYC Service Pro), analyses, workflows, and systems that I'm genuinely proud of, and I think many of them are legitimately useful.

But building products and building businesses are not the same thing.

It's remarkably easy for me to mistake activity for progress when the activity itself is intellectually rewarding. If I spend sixty percent of my week building another tool, I can convince myself I've had an enormously productive week.

The more difficult question isn't whether the tool is good; it's whether another tool is actually more valuable than another client relationship, another meeting, a property preview, or another opportunity that advances the business itself.

Of course, I know the answer.

The challenge isn't understanding what the business requires. It's consciously choosing, day after day, to do the work that grows the business rather than the work I naturally enjoy.

Many of the decisions I've made over the past year reflect that same tendency. I chose Substack because it was elegant, inexpensive, and thoughtfully designed. It gave me distribution, analytics, scheduling, and a website in a matter of minutes. It was exactly the right platform for someone whose priority was writing.

What I've gradually come to appreciate is that those priorities change once the objective shifts from publishing content to growing a business. The platform that helped me begin may not be the platform that helps me scale.

The same could be said of my decision to remain largely independent rather than joining a larger real estate brokerage. There are obvious things I sacrifice by doing so. I don't get to eavesdrop on experienced agents negotiating transactions. I don't benefit from the informal education that comes from simply being surrounded by practitioners, nor do I have the same access to technology, resources, or administrative support.

At the same time, I retain ownership over the business I'm building and the relationships I'm creating. Neither decision is objectively right; they're simply different trade-offs. Entrepreneurship, I've discovered, is little more than an endless sequence of decisions made under imperfect information.

Looking back, I think the first year of this journey was necessarily about building foundations. I built a brand. I built a body of work. I built systems. I built credibility. I built a website that I'm finally proud to point people toward, and I'm in the process of bringing more than 250 articles onto my own domain so that the work I've spent years creating has a better opportunity to be discovered.

But I don't think the second year can look like the first. The infrastructure is no longer the bottleneck.

Year Two of More For LES will not be about building the system. It will be about having more conversations. It will be about reaching prospective clients and introducing my work to people who might genuinely benefit from it. In other words, it will be about doing more of the things that make me slightly uncomfortable and fewer of the things that merely make me feel productive.

And perhaps that's the lesson for anyone standing at the edge of their own "Year Two."

I still don't know what it means to be a successful entrepreneur. But I’m ready to stop building the walls and start opening the doors.