Last week I had the chance to speak with the Oak + Pine Society in Honolulu. They asked me to talk about what I’ve learned in building, scaling, and eventually selling a business.
What you’ll read here is a written version of that talk, not every slide, short story, or Q&A moment, but the core message I shared with the room. My hope is that you can take these ideas and see yourself, and your business, in a new way.
These tools support every season of entrepreneurship: building, scaling and exiting. They include:
People — you can’t do this alone.
Principles — discipline and values turn chaos into something you can live with.
Polarity — business is a balancing act: passion and profit, vision and execution, freedom and responsibility.
A Trick Question
What do a children’s party venue and a tech startup have in common?
The answer is simple. They share the same founder.
Over a decade ago, I was building Palm Tree Playground, a children’s indoor playground and party venue. Today, I’m building a tech platform for nonfiction authors. On the surface, they couldn’t look more different. Back then I was hiring high schoolers as birthday party hosts; now I’m interviewing engineers and product strategists.
But what I’ve learned is this: the fundamentals don’t change. Whether you’re selling cake pops, code, or coaching, you still need the right people, the right principles, and the ability to hold the tensions that come with growth.
Stage One: Build with People
When we think about starting a business, it’s tempting to believe we need money first in the form of a loan or an investor. But you don’t start with money. You start with people.
Your inner circle are the voices that shape you, books, podcasts and mentors who pour wisdom into you whether you know them in person or not. These voices become your boardroom, even if you’re sitting alone at the kitchen table.
Your outer circle are the collaborators, coaches, teachers, contractors, and advisors who help move things forward. Maybe it’s the freelancer who designs your logo, the advisor who takes your call, or the friend who connects you to your first client.
Every stage of growth requires a circle of people who stretch you past the old version of yourself.
In the Build stage, you meet mentors, collaborators, and early advisors.
As you Scale, you move to high level coaches, contractors, and clients.
And when you Exit, you seek a viable buyer or successor.
Your circle is always evolving and you always want to be cultivating it.
In 2024 I wanted to meet experts, so I signed up for a challenge a month, little online programs that cost under a hundred dollars and taught me everything from public speaking to publishing. I ended up completing nineteen of them. Those experts collapsed time for me. They took things that would have taken me years to figure out and handed me the shortcuts. That’s the gift of surrounding yourself with the right people.
Dan Sullivan says it perfectly in Who Not How: “Your goals and dreams are so big they can’t be achieved alone—and that’s the point.”
The tension, of course, is that entrepreneurship is born from independence. But the very independence that gets us started can keep us stuck if we don’t let other people in. The myth of the lone genius makes a great movie but it’s not how businesses are built.
Try this today: Write down three names. One person who inspires you. One person who could collaborate with you. One person who could connect you to someone new. That’s your first team.
Stage Two: Scale with Principles
If the Build stage asks “Could this work?”, the Scale stage says, “This is working, help!”
Growth doesn’t feel like freedom at first. It feels like out of control.
When Palm Tree Playground was at its peak, Saturdays were pure madness. Twelve employees running around, back-to-back parties, parents with questions, sticky floors, balloons everywhere. I was drowning. Every decision, every complaint, every emergency still landed on my desk.
Verne Harnish writes in Scaling Up: “Growth companies don’t fail because of a lack of opportunity; they fail because they can’t handle the growth.” I couldn’t handle the growth. Not until I learned that routine, not hustle, is what actually sets you free.
We put systems in place: managers for the weekends, software to manage bookings, cleaning checklists, and peer-to-peer training so new hosts weren’t starting from scratch. The more structure we created, the more space I had to breathe.
That was when I stopped reacting and started leading.
Michael Gerber puts it this way in The E-Myth Revisited: “Great businesses are not built by extraordinary people, but by ordinary people doing extraordinary things.” And ordinary people can only do extraordinary things consistently when they’re supported by good systems.
The principles that anchored me then still serve me now:
1. Build to Sell, Even if You Never Do
From Goldman Sachs 10,000 Small Businesses, the very first lesson was exit strategy. At first I thought, why would I plan to leave something I love? But here’s the truth:
A business that can run without you is worth more and gives you your life back.
Even if you never sell, building as if you could means clean finances, documented systems, and a team that doesn’t rely on you for every answer.
2. Profit Protects Purpose
Profit isn’t the enemy of purpose, it fuels it.
Without profit, your vision suffocates under stress. With profit, you have oxygen to hire better people, dream bigger, and serve more.
Don’t pit money and mission against each other, they belong on the same side.
3. Iterate in Public
Perfection is the enemy of progress.
If you wait until your product or offer is flawless, you’ll lose speed and connection. By iterating in public, you build trust, gather feedback, and move faster.
4. Say No More Than You Say Yes
Every yes is equity.
In my early days, I wasted mine on shiny things including coupon books and quick-fix ads. Most drained my energy and brought in the wrong clients.
Now I guard my yes carefully. Because when you say no to the wrong things, you make space to say yes to the right ones.
5. Your Nervous System Is a Business Strategy
Here’s something I learned from Dr. Jen Bourgeois and Emily Judice. Most entrepreneurs ignore their nervous systems, but your nervous system is the most important business system you have.
If you’re always in fight-or-flight, you make reactive, desperate decisions. Hustle culture calls it drive. In reality? It’s burnout.
Protecting your health with rest, movement and nervous system regulation is not a luxury.
Your nervous system is a business strategy. Treat it like revenue depends on it. Because it does.
6. Act Like the Business Owner You Want to Be
Every decision you make comes from one of two places:
Your past self who kept revenue small.
Your future self who’s building the business you want.
Don’t wait for the revenue to show up to act like that person. Step into that identity now.
And here’s the polarity you’ll face in Scale: the tension between freedom and discipline. We resist structure because we want freedom, but freedom only comes through discipline. The routines you resist might be the very thing that unlocks the life you want.
Try this today: Ask yourself, what’s one area of my business where routine would set me free? Sales calls? Content creation? Write it down, put it on your calendar, and give it a week.
Stage Three: Exit by Embracing Polarity
Now let’s talk about Exit.
Most people hear “exit” and think Silicon Valley headlines: billion-dollar buyouts, founders sailing into the sunset. But for small business owners like us, exit simply means freedom. It means building something that can thrive without you.
John Warrillow says in Built to Sell: “If your business can’t function without you, you don’t own a business—you own a job.”
For me, exit came after a season of deep exhaustion. I was so tired of being the bottleneck. Ryan Holiday says in The Obstacle Is the Way: “The obstacle in the path becomes the path.”
The exhaustion forced me to see I was the obstacle in the path and I had to learn to make the business valuable without me built into every system. The new system became my exit strategy. We documented systems. We trained people to make decisions without me. We built a reputation that wasn’t tied only to my face. And when it was time to sell, the business could stand on its own two feet.
Exit asks you to embrace polarity. You love your business, but you can’t cling to it forever. You have to hold the tension between loving what you built and letting it go so it can serve more people.
Try this today: Imagine you step away for thirty days. No email, no texts, no quick check-ins. What would break first? That’s your clue. That’s the system, person, or process you need to shore up next.
In closing
In the Build stage, what you need most are people.
In Scale, what you need most are principles.
In Exit, what you need most is the ability to hold polarity.
Which stage are you in: Build, Scale, or Exit? And what’s your next move?
The 3 P’s aren’t just about business. They’re also about writing.
Every author I’ve worked with needed people. They had an inner circle of influences and an outer circle of guides to get their words on the page. They needed principles that included the structure, the discipline, and the framework to finish what they started. And they needed polarity, the courage to let their book live in the world, even when it meant stepping back from it.
That’s why I built TellaDraft. It’s more than software; it’s a reflection of this framework. People, principles, and polarity are designed right into the platform. And it’s why I created this Founders Room, a space where other entrepreneurs can hold these tensions together, in community.
Because whether you’re writing your first book or building your first company, freedom comes the same way: through the right people, the right principles, and the willingness to hold the polarities that make growth possible.
Such a great talk, Heather! I love the part where you say "A business that can run without you is worth more and gives you your life back." So many entrepreneurs don't think of their business that way. Many of them are just trying to survive each day rather than think long term. What a valuable lesson.