Starting a business is one thing. Keeping it going? That’s where the real learning happens.

At Shift, we love talking to people who build things, especially those doing it with limited resources, long days, and more open tabs than they care to admit. To celebrate Small Business Month, we reached out to five founders across industries, from wine farms to marketing agencies, to hear what it’s really like to grow something from scratch.

Whether you're just starting out or thinking about taking the leap, their insights are full of honest advice, helpful lessons, and the kind of encouragement you only get from someone who’s actually been there.

Starting with Purpose

Most great businesses don’t start with a pitch deck. They start with something smaller and more stubborn—like a feeling you can’t shake or an idea you keep scribbling on receipts.

For Joyce Yim and her siblings, the team behind Teaspoons Co, a boba café and online tea business with a tight-knit team of seven—the idea came from years of shared family memories and a deep love for boba. “Our love for boba runs deep,” Joyce said, recalling their early days working together at a neighborhood bubble tea shop and the moment they promised one another they’d open one of their own. Spoiler: they did.

Alison Bell, co-founder of the marketing agency Boleyn Media Group, now leading a team of ten, started her business during maternity leave. With a newborn at home and a husband who shared her marketing background, they decided to build something together that supported local businesses and gave them more control over their time as new parents.

Tedi Fisher, founder of The Nest Clinic, a wellness space supported by a team of fifteen, was inspired by a desire to create something nurturing and healing. Coming out of maternity leave during COVID, she envisioned a calm, welcoming space, what she describes as “a massage for the nervous system," where people could feel genuinely cared for. That blend of wellness, intention, and care became the foundation of her business.

Joanna Schlosser, co-founder of Niche Wine Co., and her partner launched their winery in 2009 with a grant and a gut feeling. “We had no grand plan, just an unwavering belief that we could do something different,” she said. Today, they run the winery with a team of four in the low season and ten in the high season, focused on farming, winemaking, and creating a welcoming space for visitors. 

Tom Rusling had spent eight years in the agency world before deciding it was time to build something of his own. “I wanted full accountability—for the strategy, the execution, and ultimately, the outcomes,” he said. That craving for clarity and control, plus the freedom to pursue long-term ideas without compromise, became the spark behind Reflexive Media, now an eleven-person team. He later launched Audience Key, too. 

Each founder started from a different place, but they had one thing in common: they built something personal, not just profitable.

The Reality of Pivots and Pressure

No matter how strong your start, things don’t always go according to plan. Every founder we spoke to had to make unexpected moves to keep their business going.

When the pandemic hit, Teaspoons had to adapt quickly. “Pivoting wasn’t just an option, it was a necessity,” Joyce told us. They launched DIY boba kits and began selling tea online, what started as a quick pivot became a whole new stream of revenue.

Niche Wine Co. faced a rough couple of years after opening a new winery and tasting room. Between wildfires, crop loss, and a deep freeze that wiped out local grapes, their team had to get creative. They leaned on their community, sourced grapes from other regions, and launched a farm-stay experience to bring in new visitors and diversify their income.

In the tech world, Reflexive Media shared how a sudden shift in Google’s search algorithm changed everything about their business model. Their entire approach to SEO had to evolve overnight, and with it, their strategy for serving clients. 

For all of them, adaptation wasn’t a side skill, it was a core part of survival.

Related Post: How to Start a Side Hustle: Real Stories from Four Hustlers

If I Could Start Over, I’d Tell Myself…

Here is some advice they’d give to their past selves if they could turn back the clock before starting it all. 

“Perfectionism kills. Done is better than perfect. Feedback beats theory,” said Tom. It’s advice he stands by after years of building and refining in the digital space.

Joyce reflected on how ambition sometimes got ahead of her resources. “Don’t spread myself too thin and focus on one project at a time. I had too many ideas and wanted to do too many things without all the necessary resources.”

Tedi emphasized the importance of staying rooted in your mission. “Keep coming back to your why,” she said. It’s a phrase that continues to guide her when things feel overwhelming or off-course.

For Alison, self-compassion was something she had to grow into. “Don’t be so hard on yourself! Every day and every exciting milestone presents new challenges, and I often need to remind myself of how much I've grown personally and professionally through this journey.”

And Joanna offered a reminder about courage and belief. “If you want to be successful, prepare to be doubted and tested... It’s not who you are that holds you back; it’s who you think you’re not.”

Redefining Success

Over time, success starts to mean something different. For these founders, it’s become less about growth at all costs and more about balance, alignment, and sustainability.

For Tedi, success used to look like external validation. These days, it’s shaped by alignment—having enough time with her patients, the flexibility to be with her family, and the freedom to grow her business at a pace that feels sustainable.

Tom said he still cares about growth, but building a healthy team has become just as important. “Eight years in, success means something very different than it did at the start. I always cared about building a good team, but now I see just how much that IS the success. Having a group of talented, respectful, no-drama people who genuinely work well together—that’s what makes everything else possible” he said. 

Alison echoed that. For her, it’s all about doing meaningful work while being present for her kids. “Success to me is fulfilling my love for what I do, with my love for my family.”

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How They Stay Organized (and Sane)

Founders wear a lot of hats. Some days, it's CEO. Other days, it’s customer support, head of IT, unpaid intern, or the person who buys toilet paper. This makes organization a top priority. For most, it’s not about doing more, but finding ways to do things more clearly and with less friction.

Tom shared the value of investing in tools and support early on—especially for the tasks he didn’t enjoy. For him, it was a way to protect his energy, stay focused, and avoid burnout. Alison echoed that sentiment from a team-building lens. “I’m grateful our agency has people in all of these roles now who are WAY better than me in any of them,” she said. “Do what you do best, and delegate the rest.” And while some rely on systems and software, Tedi’s go-to strategy is simple: unplug. Her most reliable method of staying grounded isn’t digital—it’s time in nature, whether that means a walk in the forest or quiet moments by the creek.

And when you’re wearing every hat yourself, staying organized online matters just as much as off. That’s why we built Shift: to bring your tabs, tools, and accounts into one focused workspace, so you can spend less time clicking around and more time doing what you love.

Final Thoughts: Just Start Somewhere

None of these founders started with a flawless blueprint. Some began with a single idea and a wildly optimistic spreadsheet. They figured things out as they went, adjusted when things got messy, and stayed connected to the reason they started in the first place.

Wherever you are in your journey, whether you’re sketching out ideas, launching your first product, or scaling what you’ve built, we hope their stories give you something to take with you.

And if you’re looking for a better way to manage your digital day, Shift is here to help. We built it for people like you: founders, creators, and small teams doing meaningful work who could use a little less clutter and a little more clarity.

Try Shift for free and see what it feels like to have your entire online life in one place.