Inside the Exit: Two Founders on Building, Scaling, and Selling Digital Businesses
A lot of founders spend years building something — and almost no time thinking about how it ends. The exit, when it finally comes, arrives as a surprise: messier, more emotional, and more logistically complicated than anyone warned them it would be.
At Nomad Summit in Chiang Mai, Fiona Laidlaw, Regional Director at Flippa, sat down with Sheena, founder of a decade-old activewear e-commerce brand built for pole dancers. They were, at the time of the talk, actively mid-sale. Not reflecting on a completed deal. Actually in it.
That made the conversation unusually candid.
What Buyers Are Actually Buying
Sheena's business had been running for over ten years. She'd built it from a niche she understood intimately — activewear for pole dancers that had the coverage of athletic wear and the aesthetic of lingerie. It filled a specific gap, built a loyal community, and over time developed something harder to replicate than product: brand trust.
When buyers came to the table, the product itself was almost secondary.
"The biggest thing is the brand will," Sheena explained. "It's been in operation for over ten years. It has a reputation and a legacy."
Three things stood out to buyers as genuinely valuable. First, that brand equity — the decade of community-building, testimonials, and repeat customers that a new owner could inherit immediately. Second, the supplier relationship: a manufacturer in Pakistan with whom Sheena had built trust over ten years, to the point where defective inventory was replaced without dispute. Starting that relationship from scratch carries real risk. Third, the fact that the business was running largely without her — Sheena had become a mother five years earlier and had gradually stepped back, running the operation at under ten hours a week.
Buyers found that last part particularly compelling. A business that doesn't depend on its founder isn't just easier to run — it's lower risk to acquire.
What Made the Books Messy
Here's the uncomfortable part. Sheena has a background in accounting. She knew what clean financial records should look like. And yet, when it came time to sell, her books were tangled.
"My accounts — it's so embarrassing," she said. "When you're a founder, your books are kind of mixed with your personal expenses and your business expenses."
This is remarkably common. Not because founders are careless, but because, in the early years especially, the boundary between personal and business finance is genuinely blurry. Founders optimise for points on credit cards, move money between accounts, and make decisions that are perfectly logical operationally but create forensic headaches later. Add to that the lifestyle of a digital nomad — multiple cards, multiple currencies, multiple accounts — and the P&L that buyers need to see becomes a manual reconstruction project.
Revenue was relatively clean; Shopify made that traceable. The expense side was harder. Separating what was business from what was personal took time, slowed the process, and introduced uncertainty that buyers noticed.
The fix, in retrospect, is simple: separate finances from day one. Not because a sale is inevitable, but because clean records are much cheaper to maintain than to reconstruct.
The Deal That Fell Through
The first serious offer came from an Australian buyer. Things progressed well enough for due diligence to begin. Then it collapsed — over something Sheena hadn't thought to mention.
The business was incorporated outside Australia. Sheena had been living abroad for over ten years. To her, this was just context. To the buyer, it was a dealbreaker.
"It didn't occur to me that it would be important to him that the business was incorporated in Australia," she said. "He thought, being Australian, that the business was incorporated in Australia. When it came to due diligence, he said this was too risky."
The lesson here is subtle. Due diligence isn't just financial. It's structural, legal, and psychological. Buyers have their own risk tolerance, their own jurisdictional comfort zones, their own assumptions about what "safe" looks like. Information that feels irrelevant from the seller's perspective — where the company is registered, who the team are, how the logistics actually work — can be decisive from the buyer's side.
You rarely know in advance what matters most to a specific buyer. Which means the best approach is to share everything, not just what seems relevant.
The Emotional Layer That No One Talks About
After her first call with Fiona, Sheena called her therapist.
She'd realised she was attaching her sense of self-worth to the outcome of the sale. The procrastination she'd noticed — delays in sending documents, reluctance to move quickly — wasn't laziness. It was self-protection. Selling a business you've built over ten years can feel, she said, like judgment day.
"When you sell your business, especially one you've been working on for a decade, it feels like your value is on the line."
This is rarely discussed in the tactical literature about exits. Valuation multiples get covered extensively. The psychological experience of selling something that has been central to your identity for years — that gets much less attention.
Sheena's approach was practical: she did the emotional work before the process got further along. By the time the first offer came in, she was more resilient. When that deal fell through, it was disappointing rather than devastating. She'd already separated her value as a person from the market value of the asset.
Which sounds obvious to say. But is genuinely difficult to do.
What She Leveraged in Negotiation
When Fiona suggested Sheena join buyer calls directly, she always said yes. Video presence, she found, was one of the most effective tools available to her.
"I tried to leverage me the most. The warmth that comes through on a video call, and the trust in me — I learned to leverage that."
She also made a credible commitment: she offered to stay on through the transition, to help train a new team, and to make the handover smooth. Her existing team — five people — were moving with her to her next venture, but she arranged for them to assist with hiring and training before they left.
For buyers, this mattered. Acquiring a business and then being left alone with it, without the institutional knowledge of how it actually runs, is a real fear. A seller who is visibly invested in a successful transition is more trustworthy than one who wants to close quickly and disappear.
The Founder Drift Problem
One of the more honest admissions in the conversation was about what happened to the business in the two years before the sale.
"I've been operating the business without much strategic direction, because I was thinking I'm going to sell it. I was not as motivated to make those big strategic decisions."
This is a pattern Fiona sees regularly — what she described as the five-to-eight year mark, where founders start to tire, start to drift toward new ideas, and gradually allow the business to stagnate. The problem is that this drift is visible in the financials. A declining bottom line reduces valuation. A business that looks like it peaked two years ago raises buyer questions about where it's heading.
The counterintuitive advice: operate as if you're not selling. Make the strategic decisions. Maintain the profitability. A business that's performing well sells better and sells faster.
And if you're thinking about selling, talk to a broker sooner than feels necessary. Sheena's repeated refrain was that she wished she'd connected with Fiona five years earlier — before her motivation as a founder had dipped, before the financials had softened, before the process felt urgent rather than strategic.
Current Market Multiples
For those wondering where valuations currently sit, Fiona offered a brief read on the market:
- B2B SaaS is still attracting strong multiples — roughly 4–5x EBITDA
- Content businesses are under pressure from AI and declining Google reliance — closer to 1–3x
- E-commerce sits around 2.5–3.5x, depending on the business quality and scale
These aren't fixed. Business type, revenue quality, operational independence, and market conditions all move the number. But as a rough orientation, this is where the market is.
Build as If You'll Sell, Even If You Won't
The closing advice Sheena offered was aimed at founders earlier in their journey than she was.
"I would always build with the goal of selling. Even if you don't plan to sell, how you build should always have the foundations and the infrastructure necessary for a sale."
Clean finances. Documented systems. A supply chain that makes sense to someone who didn't build it. A brand that doesn't depend entirely on the founder's presence. A business that runs without daily intervention.
These aren't just exit requirements. They're the markers of a well-run company at any stage. The businesses that are easiest to sell tend to be the ones that are also the most resilient, the most scalable, and the most enjoyable to run.
The exit, when it comes, should feel like a natural conclusion — not a scramble to make something presentable. That takes years of small decisions made well before any buyer appears.
Sources & References
- Flippa — online marketplace for buying and selling digital businesses, apps, and websites