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June 3, 2025

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Do you go for a run before putting your shoes on? Checkout before selecting your groceries? Celebrate your kid's graduation before they're in school?

Obviously not.

So, then, why do we try skipping steps when building our businesses?

Every startup follows the same journey. The timelines can vary wildly — Joel Gascoigne validated Buffer in a month, while Eric Simons spent seven years on StackBlitz before things really clicked.

But the phases are always the same.

In my experience, this happens because most founders think they're further along than they are; largely because they don't know what evidence to look for to verify where they're at.

They're building an MVP before validating the problem. Seeking product-market fit when no one's paid them yet. Looking to scale before understanding what customers are paying for.

This confusion is expensive. You end up solving the wrong problems, at the wrong time.

So, let's straighten things out.

In this newsletter:

• The five phases every startup goes through

• A 6-question diagnostic to confirm which phase you’re in

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Weekly Insight

Quick note for part-timers: the timelines I provide assume full-time hours (~40/week). Working 10 hours/week? Adjust accordingly. A 3-month phase becomes a year, and that's completely fine. Progress is progress.

Phase 1: Problem discovery 

You're here if you're still figuring out what specific problem you're solving and for whom. Maybe you have a vague idea (“productivity for entrepreneurs!”) but can't explain the exact pain point in one sentence.

What to solve for

You need to ensure the problem you’re tackling is important enough, to you, that you’d want to spend years of your life working on it. Things typically happen more slowly than you’d like, so be prepared to commit to this thing for the long haul—when it’s boring, unsexy and not moving forward. 

⚠️ Your resolve will likely never be as strong as it is when first committing to the idea, so be mindful of that in your decision-making ⚠️

Realistic timeline

1 month of talking to actual humans, doing research and internalizing the reality of solving this.

Phase 2: Solution discovery 

You know the problem cold. You could write your customers' complaints better than they could. Now you're building something—anything—that solves it. (even if it's held together with duct tape and prayers)

Don't worry about getting things perfect; they will change as you go forward. Your goal here is to test solutions to the problem you've identified in step 1. Ideally, you're going to come up with realistic solutions you could execute on, then return to those you interviewed initially to see what they think.

What to solve for

Getting someone to actually pay you. Not “would” pay. Not “might” pay. Pulling out their credit card and giving you money.

Because, here’s the thing. People lie. Not maliciously—they want to support you. When you show them your idea, they'll say encouraging things like “I could see myself using this!” or “That's super useful!”

But nice doesn’t pay the bills.

The only validation that matters is when someone trades their hard-earned money for your (imperfect) solution. Until then, you're still guessing.

Realistic timeline

3–4 months to build a solution people find valuable enough to buy.

Phase 3: Product-market fit 

You've got paying customers. Great! That deserves a lil’ happy dance… then back to work.

If I had to use one word to summarize the first 3 phases, it’s skepticism. In order to succeed, you need to be skeptical of tomorrow’s success.

You need to find out if your customers love what you've built, or if they’re just throwing you a bone. You’re aiming for customer feedback like “I can't work/live without this.”

What to solve for

Getting 40%+ of users to say they'd be “very disappointed” if your product disappeared tomorrow. This is the magic number that separates real businesses from side projects. (I explained what 40% has to do with anything in a previous newsletter)

Realistic timeline

6–9 months of constant iteration based on user feedback.

Phase 4: Traction 

You've built something people genuinely love. Congrats, because that’s hard. 👏🏼

But I have bad news. This doesn’t necessarily mean you have a business. 

To get there, you’ll have to adjust your watch to marketing time.

Growth is unpredictable and customers churn for all sorts of reasons. If you want your business to succeed, you need predictable sources of new customers—both to replace those who leave and to actually grow revenue.

⚠️ This is the phase most people waste time thinking about before they're ready. If you haven't nailed the previous 3 phases, slow down. There's no point building go-to-market strategies when you should be perfecting your product. ⚠️

What to solve for

Predictable customer acquisition. You need to know that if you put $X into a channel, you'll get Y customers out.

Focused experimentation is the name of the game. Make concentrated plans (and I mean write it down) to test out each channel. 

Realistic timeline

9–12 months of constantly testing channels, to find one that really works.

Phase 5: Systems 

You've found product-market fit. Customers love you. Revenue is predictable. Now, finally, you have a business. Cue the sigh of relief.

It can be tempting to take your foot off the gas here, but you’d be doing yourself a disservice. It’s more than likely that you’re critical within the business at this point. If you want to optimize life for freedom and enjoyment, you need to work on business design. 

Build the machine that runs without you—processes, documentation, maybe even (gasp) employees.

What to solve for

Can the business survive a week without you? If you disappeared tomorrow, would customers still get served, bills still get paid and growth continue?

Realistic timeline

6–12 months to build foundation, then continuous improvement… forever (or, at least, until you sell the business).

📚 Related Reading

• Overcome shiny object syndrome by Kelly Snodgrass

• The productivity paradox by Simon Litt (that’s me! 🙋🏻‍♂️)

• Integrating customer focus in product development by the Digital E team

Intent to Action

Phew, okay, that was a lot of info. I want to ensure I’m actually helping you, not just further confusing you.

Thus, a simple checklist.

In my experience, it’s really hard to be objective about the phase of business we’re in. So, I created this simple little questionnaire to answer for you.

Can you explain your customer's problem in one sentence?

• No → You're in Phase 1

• Yes → Continue

Has anyone paid you money?

• No → You're in Phase 2

• Yes → Continue

Is the solution they paid for scalable?

• No → You’re sticking around Phase 2

• Yes → On you go

Would 40%+ of your customers be “very disappointed” if your solution disappeared?

• No/Don't know → You're in Phase 3

• Yes → Continue

Do you have predictable customer acquisition?

• No → You're in Phase 4

• Yes → Continue

Can your business run without you for a week? A month? A year?

• No → You're in Phase 5

• Yes → Congrats, you've built yourself a great life!

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Closing Thought

It's tempting to work on the fun stuff. The rebrand. The AI feature. The podcast.

But successful businesses aren't built on what's exciting. They're built on doing the boring, difficult, necessary work for your current phase.

So this week, be boring. Do the work that’s actually going to move you forward.

Your future self will thank you.

Next week, I’m revisiting the concept of a minimum viable product. Where the old-school wisdom holds, and where the idea needs to adapt in order to succeed in our “ever-evolving world.” 🙃

See you then.

PS: Hit reply and tell me which phase you're in. I read every email and love hearing where you're at in the journey. Especially if you thought you were somewhere else before taking the quiz. 😉