Bootstrapping a SaaS MVP isnāt just a coding sprintāitās a mental grind.
As a Senior Software Engineer at Microsoft (after Clear Softwareās acquisition) and through side projects like Spare Cloud and SitePixel, Iāve stumbled plenty. Each project left me with hard-learned lessons about what not to do.
Here are six mental hurdles I hitāand how I overcame them.
1. Ship first. Polish later.
At Clear Software, I wasted days building AS400 integration⦠only for it to get scrapped when we doubled down on SAP customers. In my side projects, I burned hours polishing UIs for features that never shipped.
The problem: perfectionism kills progress.
The fix: I now use a Kanban board for side projects where I ruthlessly focus on the smallest possible amount of functionality needed to solve the problem. At Clear Software, we nailed one SAP integration first before expanding.
2. Chasing Non-Business Tasks
I once spent days hunting down and setting up analytics tools for a project with zero users because I wanted the best setup. At Clear Software, I tinkered with logging systems instead of helping my team better optimize our products and delivery for customers.
The problem: users donāt care about your tech stack or tools.
The fix: focus on tasks that directly provide value.
- Focus on adding a super simple logging mechanism, or use provided tools, like Cloudwatch in AWS.
- Run weekly 15-minute reviews: āDoes this task help me provide users real value or move toward revenue?ā
If not, it goes in the āLaterā pile.
3. Thinking a Product Is a Business
My Spare Cloud backup service had a slick UI and backend. I thought I was golden. But with no users and no revenue, it was just⦠code.
Even at Microsoft, acquisitions like Clear Software only mattered because there was a business model attached.
The fix: plan business with product.
- Define your customer.
- Test pricing early.
- Put your product into the hands of usersāeven those outside your initial target audience.
At Clear Software, we moved quickly to get our product in front of more people. That accelerated our learning and made our product more useful. Sometimes it was evolving how we used our own product, not just manipulating the codebase.
4. Validate or fail fast.
I used to keep ideas secret, worried about people stealing them. A few project's flopped because I never validated with real people.
The problem: ideas in your head donāt count.
The fix: share early, validate often.
- Sometimes I get feedback through social channels onlineāfeedback saved me weeks of wasted coding.
- More often, I validated by asking my stakeholders directly.
- Shy? Start with a simple Google Form.
5. Your first 10 users matter more than your first 10 features.
I thought good products sold themselves. Wrong. Most of my side projects fizzled because I had no outreach or distribution plan. At Clear Software, sales and marketing turned our tech into an actual business.
The fix: treat distribution like coding.
- Schedule weekly progress check-ins with peers or mentors to hold yourself accountable.
- Send cold emails weekly.
- Spin up a simple landing page so people have somewhere to go.
Your first 10 users matter more than your first 10 features.
6. Overvaluing My Engineering Effort.
SitePixel, my feedback widget, had two paying customers. Someone once offered me $5,000 to buy it. I refused, thinking the engineering effort Iād poured in made it worth more. I eventually lost both customers, shut it down, and pocketed less than $5k.
The problem: I confused my effort with actual value.
The fix:
- Understand what value really means (to you and to others).
- Accept that value looks different depending on perspectiveāyour hours coding donāt automatically translate to customer or market value.
- Negotiate with a clear head, not with your ego.
Keep Building
Bootstrapping is a head game. To survive it:
- Avoid perfectionism.
- Focus on real user value.
- Plan beyond just code.
- Validate ideas early.
- Prioritize distribution.
- Understand and negotiate value clearly.
Between Clear Software, Microsoft, Spare Cloud, and SitePixel, I learned these lessons the hard way. You donāt have to.
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