What was the hardest thing you've experienced in business?

For me it's not one hardest thing, it's that I never get the luxury of having just one. I run three businesses at once, and each one has its own version of "the thing that quietly blows up if nobody catches it." The actual hard part isn't any single problem, it's deciding whose fire to put out first when I've only got one brain and one morning. I spent almost 30 years advising other companies on exactly this failure mode before I became my own case study running a software company, a care home, and a cafe at the same time.

From what I’ve observed, scaling seems harder than starting. A small team can build something people like, but turning that into repeatable acquisition, reliable operations, good hiring, and disciplined spending is a completely different challenge. That’s one reason why I find VC accelerators (like that of 1752vc) helpful, because they focus heavily on mentors and operating support alongside fundraising—the check alone doesn’t solve the scaling problem.

The hardest thing I've had to overcome while building my platform has been organization. Before I even started building anything from the ground up, I would just follow tutorial after tutorial, and it felt like I wasn't really getting anywhere. After watching quite a few, I started building from scratch and doing my own research on various topics or issues I came across. Throughout the process, file organization became easier and less daunting. When following tutorials, they manage the files for you, making it harder to organize your own project when the time comes. Don't get me wrong, watching tutorials can be helpful, just make sure to apply what you learn to your own project.

Mine was almost shelving something I'd already put months into. I'm 30 years into organizational development work, and a couple years ago I was running a software company, a care home, and a cafe at the same time, mostly to stress-test an AI tool I was building to help me keep track of all three. Right before launch it gave me a benchmark result that looked bad enough that I nearly killed the whole project. Turned out the tool was right to flag it as low-confidence rather than quietly hiding it, and that "I'm not sure, check this" instinct became the actual product. The hardest part wasn't the technical problem, it was almost throwing away something good because I couldn't tell the difference between "this is broken" and "this is honestly telling me it doesn't know yet."

For me it's not one moment, it's the constant low grade fatigue of deciding which business needs me right now. Software company, care home, cafe, they all compete for attention equally even though they're not equally urgent. I ended up building FounderFlow because of this (I'm the founder, disclosing since it's directly relevant), but even before that existed the real fix was forcing myself to write down what actually counts as "off" for each business instead of reacting to whatever felt loudest that hour.

The hardest thing I have ever had to do in business honestly in NOT to undersell myself. I had customers. The product was great but I always had this fear that they would go elsewhere or just not hire me if my prices were too high. Not too high for the product or service but high for them. I lost a lot of money that way.

Hardest thing for me was realizing hours worked had stopped meaning anything once I was running three businesses at once. I could work a 14 hour day and still miss the one thing that actually mattered because I was scanning instead of deciding. That's the whole reason I built FounderFlow, full disclosure I'm the founder. Took me too long to admit the problem was attention, not effort.

For me it was the moment I realized I could not keep the business in my head anymore. Everything ran fine on memory and a notebook until there were three clients, two hires, and a dozen small promises in flight at once. Nothing dramatic broke, tasks and follow ups just quietly slipped, and I did not notice until a client mentioned they were still waiting on something from three weeks earlier. Scaling past what one person can hold in their head is a different problem than anything I had solved before.

For me it was realizing that watching my businesses closely and watching them well weren't the same thing. I could tell you every number, but I still missed the quiet stuff, a lead going cold, a task nobody owned, until it became expensive. That gap is basically why I started building FounderFlow.

For me, the hardest thing has been the silence between shipping and traction.

I just launched my first product today (a free online party game called Salad Bowl Game), and the emotional rollercoaster is real:

🎢 The high of hitting "publish" — everything feels possible, you're proud, you check analytics every 5 minutes...

😶 The silence that follows — hours pass, maybe a few visitors, but nobody's engaging. You start questioning every decision: "Is the product actually good? Did I pick the wrong day? Is my description unclear?"

🔥 The second-guessing spiral — Should I add feature X? Change the landing page? Post on more platforms? Or is the problem deeper?

What I'm learning: The gap between "it works" and "people care" is where most indie builders quit. Not because the product is bad, but because the silence feels like failure when it's actually just... the beginning.

The hardest part isn't building. It isn't even launching. It's staying motivated when the world doesn't immediately notice — and not making panicked decisions out of insecurity.

To anyone reading this who's in that quiet phase right now: keep going. The fact that you shipped already puts you ahead of 90% of people who never will. 🙌

Curious what others' experiences have been — was it the technical challenges, the business side, or something else entirely?