Episode 3 | Building a Business Your Life Can Actually Hold

What Jazmin Portnow’s 13 Years of Entrepreneurship Taught Her About Staying Power

There’s a version of entrepreneurial success that looks really good from the outside.

The calendar is full. The revenue is there. The business is moving. By every visible measure, things are working. And yet something underneath feels off. The business is growing — but it’s also getting heavier. Harder to carry. Further from the reason you started in the first place.

Jazmin Portnow knows that version of success well. She lived it. And in Episode 3 of Founding Well, she tells the unfiltered story of what it cost her — and what it took to build something different.

How She Started, and What She Didn’t Plan For

Jazmin didn’t launch her business with a vision board and a five-year plan. She followed her husband to Charlottesville when he started his PhD at UVA, found herself home at 5:15 every evening with no commute and no plan, and thought: there are a lot of wedding venues here. Let’s see what happens.

What happened was that the business worked. Word spread. The snowball effect was real. When they relocated to the DC area, she kept a team in Charlottesville because the market was too strong to leave. She expanded. She grew. And somewhere in those first few years, a side income became a career — whether she fully planned for it or not.

But here’s what she’s honest about: the business grew faster than the foundation did. She was building on momentum before she was building on structure. And for a while, she could carry it.

The Year Everything Was Too Much

The breaking point didn’t come quietly.

When COVID hit, Jazmin was two weeks pregnant with her first child. The wedding industry didn’t collapse, it postponed. And then when the world opened back up, two seasons worth of weddings landed in one calendar year. Couples who had postponed. Couples who were newly engaged and ready to celebrate. All of them, at once.

She did approximately 35 weddings herself that year. With a newborn. She describes it as the most financially successful year of her career to that point — and the year she was most miserable.

“The most financially successful year in my business turned out to be the one I was most miserable during.” -Jazmin Portnow

She also didn’t know she was pregnant with her second child until she was four months along, because she was so disconnected from her own body. Eating gas station food at 1 a.m. after weddings. Running on adrenaline and obligation. Not stopping long enough to notice what was happening.

The clarity finally came in a closet. Three and a half weeks postpartum, back at work for a difficult client she felt responsible for, during an event that went sideways in ways beyond anyone’s control. She found a quiet corner, sat down, and had a full breakdown. And in the middle of it, the thought that crystallized everything: if I had a corporate job, I would still be on maternity leave. What am I doing?

The Rebuild: Systems, Team, and Letting Go

The turnaround wasn’t immediate. Jazmin is clear about that. She had commitments already on the books. She had a team that needed training. She had to learn, slowly, how to sell her team instead of herself, which is its own kind of difficult when clients come to you specifically.

What shifted first was the way she thought about the business. She started treating it as something bigger than her, something that could exist and run without her being at the center of every event. That reframe unlocked everything else. If the business didn’t have to depend entirely on her, then it could be documented. Systemized. Handed off.

She built the processes. She trained the team thoroughly. She assigned smaller weddings to her planners and supported them through it. And then she started assigning bigger ones. And then she started stepping back further.

“Where you are weak, maybe somebody else is strong. That’s the strength behind building a team.” -Jazmin Portnow

It took about a year and a half to two years before she felt genuinely comfortable stepping away. Now, she sometimes forgets there’s a wedding happening on a Saturday. Not because she doesn’t care but because she built a team she trusts completely.

The Patterns That Start Early

Jazmin’s story is 13 years in the making. But the lessons she shares aren’t only for founders who are already deep in it. They’re for founders who are still at the beginning because the patterns that led to her breaking point started early.

The belief that only she could do it right. The resistance to documentation because there was always something more urgent. The willingness to push through discomfort because the business needed it. These aren’t character flaws, they’re survival strategies that work beautifully in the early days and become liabilities over time.

She also said something toward the end of the conversation that I haven’t stopped thinking about: nothing in your business is permanent. What you build, you can change. If something no longer serves you, you don’t have to keep it just because you invested in it. Fail faster. Pivot. That’s the whole reason you built something for yourself.

“Don’t double down on the failure just because you put some energy behind it. Change it. That’s the whole reason we started a business, so we can make those decisions for ourselves.” -Jazmin Portnow

A Question Worth Sitting With

Jazmin started her business with a clear intention: time flexibility. So that when her kids came, she’d be present. The business pulled her away from that for years. But she found her way back to it — because she knew what she was building toward.

That’s the thread I want to leave you with. Not a warning. Not a prescription. Just a question.

Is the business you’re building right now something your life can actually hold?

Because momentum is real and necessary. But it’s not the same as staying power. And the earlier you start asking that question, the better.

Listen to Episode 3 | Apple | Spotify

You can listen to the full conversation with Jazmin wherever you get your podcasts. If this episode resonated, share it with a founder who needs to hear it.

Follow Jazmin: anyventeventplanning.com | beyondthebustle.com | charlottesvilledayofweddingcoordinators.com 

@anyvent_event_planning, @beyond_the_bustle and @charlottesvilledayof on Instagram