In 2022, SmugMug acquired This Week in Photo. The deal closed, money changed hands, and suddenly I went from “podcast founder” to “entrepreneur who sold a media company.” It sounds clean when you say it like that. The actual process? Way messier, way more emotional, and way more educational than I expected.
People ask me about the acquisition a lot. What was the process like? How do you even value a podcast? Would I do anything differently? So let me pull back the curtain and share what I actually learned from building and selling a digital media company.
The Real Story: We Weren’t Looking to Sell
Here’s the first thing people get wrong about acquisitions: they assume you spend years positioning your company to be acquired, grooming it for sale, optimizing everything for maximum valuation.
That’s not how it happened for us.
We built TWiP to serve the photography community. We focused on creating value—real, genuine value—for photographers who needed honest conversations about the business side of their craft. The acquisition was a byproduct of that focus, not the goal.
SmugMug reached out to us. They’d been watching what we built, saw the community we’d developed, and recognized that TWiP aligned with their vision for serving photographers. The conversation started organically, not through some strategic exit plan.
That taught me something crucial: build for value, not for exit. If you focus on creating something genuinely valuable, opportunities emerge. If you focus on the exit, you’re building the wrong thing.
Valuing the Intangible: How Do You Price Community?
One of the hardest parts of the negotiation was putting a number on things that don’t show up on a balance sheet.
TWiP had tangible assets—podcast archives, website traffic, email lists, sponsorship contracts. But what SmugMug really valued was the intangible stuff: community trust, brand equity, relationships with listeners, influence in the photography space.
How do you price trust? How do you value the fact that when TWiP recommends something, photographers listen? There’s no formula for that.
What I learned:
- Community is your moat – In a digital world where content is cheap, genuine community relationships are the real asset
- Document everything – Engagement metrics, retention rates, community sentiment—track it all, even if it feels soft
- Tell the story – Numbers matter, but so does the narrative of what you’ve built and why it matters
- Know your leverage – We weren’t desperate to sell, which gave us negotiating power
The Due Diligence Process: Prepare to Get Naked
Due diligence is where the buyer examines everything about your business. And I mean everything. Financials, contracts, intellectual property, operational processes, legal compliance, technical infrastructure.
It’s invasive. It’s exhausting. And it’s absolutely necessary.
We spent months gathering documents, answering questions, explaining decisions we’d made years earlier. Every contract had to be reviewed. Every revenue stream examined. Every operational process documented.
What I wish I’d known:
Start organizing early. Even if you’re not planning to sell, keep your business documents organized. It’ll save you months of scrambling later.
Have good advisors. I worked with lawyers who specialized in M&A and accountants who understood digital media valuations. They were worth every penny.
Be honest. If there are problems in your business, disclose them early. Buyers will find them anyway, and discovering issues late kills deals.
Protect your energy. Due diligence happens while you’re still running the business. You need systems in place so the company doesn’t fall apart while you’re dealing with acquisition stuff.
The Emotional Rollercoaster Nobody Warns You About
Here’s what nobody tells you about selling a company you built from scratch: it’s weirdly emotional.
I started TWiP in 2008. For 14 years, it was part of my identity. It was the first thing I thought about in the morning and the last thing at night. And suddenly I’m negotiating to hand it over to someone else.
The process triggered every insecurity:
- “Are we asking for too much?”
- “What if they walk away?”
- “What if we’re leaving money on the table?”
- “What happens to the community if this goes wrong?”
- “Who am I if I’m not the TWiP founder?”
The emotional stuff hit harder than I expected. Some days I was excited about the possibilities. Other days I felt like I was betraying the community or giving up something precious.
What helped:
Talk to other founders who’ve exited. They get it. They’ve been through it. Their perspective kept me sane.
Remember why you’re doing this. The acquisition had to serve the community, not just my bank account. That clarity helped during tough moments.
Protect the community. We negotiated terms that ensured TWiP would continue serving photographers. That gave me peace of mind.
The Numbers Game: What Actually Matters
People always want to know: “What multiple did you get?” or “How much was it worth?”
I’m not going to share specific numbers—that’s between us and SmugMug. But I can share what factors actually mattered in the valuation:
Recurring revenue beats one-time sales. Our membership program and sponsorship contracts were more valuable than individual product sales because they were predictable.
Growth trajectory matters. Buyers don’t just look at current revenue—they project future potential. Our growth story was compelling.
Defensibility counts. What makes your business hard to replicate? For us, it was community relationships built over 14 years.
Clean financials are worth money. Organized books, clear revenue streams, documented expenses—buyers pay more for businesses that are easy to understand.
Strategic fit multiplies value. TWiP was worth more to SmugMug than to most buyers because it fit their existing photography ecosystem.
What I’d Do Differently
Hindsight is annoyingly clear. Here’s what I’d change if I could do it again:
1. Document systems earlier
I ran a lot of TWiP processes in my head. Documenting them earlier would’ve made due diligence easier and made the business more valuable.
2. Build in recurring revenue from day one
We added membership programs later. Starting with recurring revenue would’ve made valuation easier and the business more stable.
3. Keep cleaner books from the start
Early-stage messiness is normal, but it comes back to haunt you in due diligence. Start with good accounting practices.
4. Build relationships with potential acquirers early
Not in a transactional way, but genuine relationships. It makes conversations easier when acquisition talks start.
5. Have advisors lined up before you need them
Finding lawyers and accountants mid-negotiation adds stress. Build those relationships early.
Life After the Exit: What Actually Changes
The acquisition wasn’t a finish line—it was more like clearing the deck to build what comes next.
What changed:
- Financial freedom – The pressure to make TWiP profitable every month disappeared
- Mental space – I could think longer-term about what to build next
- Validation – Proof that the community-first approach actually works
- New opportunities – Resources to launch MediaBytes and other projects
What didn’t change:
- The work – I’m still building, still creating, still serving the photography community
- The identity – I’m still a creator and entrepreneur at heart
- The mission – Helping creative professionals build sustainable businesses
Real Advice for Founders Thinking About Exits
If you’re building something and wondering about exit strategies, here’s what actually matters:
Build something valuable, not something sellable. Focus on serving your customers, building genuine value, and creating something that matters. Acquisition opportunities follow value.
Be patient. TWiP took 14 years from launch to acquisition. Quick flips are rare. Sustainable builds take time.
Know your why. Why would you sell? What would you do after? Be clear on this before negotiations start.
Get good advisors. Lawyers, accountants, and advisors who’ve done this before are essential. Don’t cheap out here.
Protect what matters. For us, that was the community. Figure out what you’re not willing to compromise on.
Don’t let it define you. Whether you exit or not, you’re still a builder. The acquisition is one chapter, not the whole story.
The Bottom Line
Selling TWiP to SmugMug taught me that exits aren’t neat, they’re not purely financial, and they’re not endpoints. They’re transitions—messy, emotional, educational transitions that open doors to new possibilities.
The best part? The acquisition validated something I’ve always believed: if you focus on creating genuine value and serving your community well, the business outcomes follow. Not overnight, not easily, but eventually.
Fourteen years from launch to acquisition. Thousands of episodes. Hundreds of thousands of listeners. One community that changed my life.
Was it worth it? Absolutely. Would I do it again? In a heartbeat. Would I do it the same way? Probably not—but that’s the whole point of learning.
