Many founders believe that starting a business with a friend is the ultimate advantage. I did too—until it cost me both my company and my closest relationship.
The hardest conversation of my life wasn’t with an angry client or a tough investor. It was with my friend, across a small table at the same café where, just a year earlier, we’d sketched our business plan on a napkin.
“I can’t do this anymore,” he said, not meeting my eyes. “This isn’t what we agreed on.”
My heart sank. He was my first business partner and one of my closest friends. And he was right. I was changing the plan. But I was trying to save our business; he felt like I was betraying our dream.
That conversation was the end of our partnership and, for a long time, our friendship. It was also the day I learned the hardest and most important lesson in entrepreneurship: the battles you fight with people are nothing compared to the battles you must first win within yourself.
The Optimism Before the Storm
When my friend and I co-founded our first bookstore in 2012, I believed our bond would make us unstoppable. We were confident in our friendship and our shared dream: to be a broad, creative publisher. We wanted to give local artists and writers a voice—publishing everything from fiction to cookbooks, just as we’d sketched on that napkin.
When Friendship Meets the Fire
For the first six months, we celebrated every tiny win. But by the one-year mark, the reality was brutal. Our initial plan—publishing a wide range of books—was failing miserably. Our resources were stretched thin, our brand was confusing, and we were bleeding money.
I dove into the hard data. The numbers were screaming that our “dream” was a sinking ship. The only part of our business with any hope was a small, overlooked category: classics and educational books. I realized we had to pivot. Hard.
I went to my friend, my partner, and laid it all out. “We have to stop publishing fiction. We have to stop cookbooks. We need to focus 100% on this one niche to survive.”
He was horrified. “That’s not what we agreed on,” he said. “This isn’t the dream. We started this to help local artists, not just sell textbooks.”
To me, he was being fearful and ignoring the data. To him, I was being reckless and betraying our shared soul. Every conversation became a battle. The trust that had been our foundation began to crack. He saw me as a steamroller; I saw him as an anchor.
The Real Lesson: The Battle Within
I pushed forward with the pivot. I was so focused on the data and survival that I failed to focus on the person sitting next to me. I didn’t honor his attachment to our original dream. I didn’t find a compromise. I chose the business over the friendship.
The tension was unbearable. That’s when we had that final, heartbreaking conversation at the café. He walked away.
Losing that friendship was a failure far greater than any financial loss. And on my own, I couldn’t save that first version of the business. It failed completely a few months later, just as my “About Me” page says.
But when I rebuilt Wardoh Books from scratch, I used that exact pivot to “classics and educational books”—the one that had cost me my friend—and this time, it worked.
What I Do Differently Today
That painful experience became my guide. Today, I build my business on these hard-won principles:
- Shared Vision is Non-Negotiable: I no longer partner with people based on friendship alone. I partner with people who share the same vision and, just as importantly, the same appetite for risk.
- Difficult Conversations Must Happen Early: I don’t avoid conflict anymore. I address disagreements head-on, with respect, before they can fester into resentment.
- Empathy is My Most Powerful Tool: I try to understand the fears and motivations of my team and partners. Success is a team sport, and a leader who doesn’t care for their team will eventually stand alone.
I haven’t spoken to that friend in years. I hope he is doing well. I succeeded in business, but I failed in that relationship. And it is a lesson I will carry with me forever.
