Founder Learning Phases: Normalizing the Journey

Jul 02, 2025

Getting something going from 0 to 1 is pretty much driven by mental resilience and grit. The Founder’s mental software is the strongest signal at pre-seed/seed. That’s why I spend time to understand you at the chain of thought. Building a unicorn isn't a linear path – it's a series of learning phases, each demanding different mental adaptations.

By understanding the typical learning phases founders experience, I can not only better identify promising entrepreneurs but also better support them through each transition. Let me break down what I've observed in each phase:

1. Messaging Phase

Mental Software Requirements:

Core System Prompt: Must be anchored in solving a real problem
Belief Network: Requires strong conviction despite minimal external validation. The conviction is stronger if it’s specific to their domain expertise.
Attention Allocation: Focused on language precision over feature development

During this phase, founders are defining the language that will shape their product and company. The best founders understand that language comes first – not the other way around. While most founders rush to build features and then "put language on it," exceptional founders realize that the exact words they choose to describe their product tells both themselves and their users what they're doing. Your language defines your focus, direction, and relevance.

I evaluate founders in this phase by observing how precisely they can articulate their value proposition and how deeply they've thought about their users' psychology.

Practical tips for founders -> I’ve seen conferences work really well for finding high user density and having a lot of experiments on messaging, set a target of the number of conversations you must have before you return home.

2. Hiring Phase

Mental Software Requirements:

Social Interface Protocol: Ability to attract top talent with limited resources
Value Framework: Willingness to delegate significant authority to early hires
Feedback Processing: Open to reshaping ideas based on new team input

Here, founders must transition from individual contributors to team builders. The quality of early hires fundamentally shapes a company's trajectory. Great founders in this phase demonstrate excellent judgment in people, investing time in developing the leaders they bring on, and delegating real responsibility. They understand that hiring is not just about filling roles but about finding partners in their mission.

I look for founders who prioritize character and alignment over skills alone, who are honest about gaps in capability, and who can articulate clearly what they need in teammates.

Practical tips for founders -> Before you start hiring, sit down with your cofounder and write a list of the things both of you appreciated in people you worked with and those that you did not. That is your company culture, even if you don’t have a team. As you are hiring, evaluate which employees are doing the best and update your guide on filtering for culture in the hiring process. In my experience of seven years as an investor in the Bay Area, I’ve rarely seen a hire mismatch because of lack of technical ability, it often comes down to culture.

3. Building Phase

Mental Software Requirements:

Belief Network: Strong technical intuition or product vision
Attention Allocation: Balances vision with execution details
Emotional Architecture: Handles feedback without becoming defensive and updates belief network based on data and not speculation

This is where the rubber meets the road. Founders must transform ideas into working products, often with limited resources. The strongest founders during this phase maintain a balance between vision and pragmatism. They're in the details without getting lost in them, and they can course-correct without abandoning their core mission.

I evaluate founders by assessing their understanding of technical tradeoffs, their ability to make smart scope decisions, and how they manage the tension between speed and quality.

Practical tips for founders -> if you have many passionate people who are ripe with ideas, but you lack a leader who built enterprise products before, your product will bloom in a thousand directions. Often individual contributor founders get this step wrong. Stay razor focused on the simplest version of your product to get you to the next stage - e.g. 100 users, 1000 users, a funding round. Do not build something in if its not a game changer for users early on.

4. Selling Phase

Mental Software Requirements:

Core System Prompt: Deep empathy for customer needs
Social Interface Protocol: Ability to build relationships with early adopters
Emotional Architecture: Resilience in the face of frequent rejection

During this phase, founders must secure their first customers – often without a fully-baked product.

Great founders don't just sell features; they sell a vision and relationship. They understand their customers' psychology and can position their product as a crucial solution to a pressing problem. It helps if you are selling to people in the domain that you are an expert in. e.g. a doctor selling to hospital execs.

I look for founders who actively listen to prospects, who can adjust their pitch based on feedback, and who show genuine curiosity about customer needs.

Practical tips for founders -> engineer founders typically will try to postpone monetization as long as they can, they’d rather build instead of selling. Then they’ll try to hire an SDR which will often not work. Only by time pressure will they try to sell and then it might be too late. Every person can learn to sell. I am an ML engineer by background, and I know the mindset, but also that helped me develop a framework/psychology that resonates with other fellow engineers and have seen founders go from zero to closing six figure contracts and loving to sell so much. This topic requires an own blog post in itself.

5. PMF/~1M ARR Phase

Mental Software Requirements:

Feedback Processing: Can identify patterns in customer adoption
Value Framework: Willingness to narrow focus to double down on what works
Belief Network: Ability to distinguish signal from noise in market feedback and update the belief network itself

This phase feels like standing at a fork in the road. One path leads to scaling; the other, to slow decay hidden behind early revenue. At ~$1M ARR, founders are often tempted to believe they've "made it." But the truth is: none of this stuff matters unless two deeper forces are working in your favor:

You're playing in a massive market.
You're driven enough to refuse giving up when it gets hard.

Even great execution can’t turn a puddle into an ocean. If early traction suggests you’re fishing in a small pond, then don’t spend years building a palace around it — jump ponds. The best founders stay loyal to solving a customer pain — not loyal to their first wedge if it points to a tiny addressable market.

I evaluate founders by their understanding of their key metrics, their iteration velocity, and their ability to make tough decisions based on market feedback.

Practical tips for founders -> if you can get to $250k/$500k, you can get to a million. Pay attention to where you’re getting the most heat with customers and going after that customer segment I’ve seen work really well. For developer tools, I’ve also seen it work well hiring a Developer Relations person, but not one who did the job before, but one who is a passionate user in your slack channel/community who kinda already behaves like a Developer Relations/Advocate for your product without being paid.

6. Founder Sells Assisted by Team <$30M ARR

Mental Software Requirements:

Social Interface Protocol: Can build and lead a sales organization
Attention Allocation: Shifting focus from product to distribution
Core System Prompt: Evolution from builder to leader

Getting to $1m ARR is the stage where VCs invest more money so founders think they have the funds and expectation to hire a sales team, but it's really just wasted effort. The goal of a sales team <$30m ARR should be to amplify the founder's ability to sell, not have the team separately sell. Until $30M ARR, sales is just doing basic order taking. Exceptional founders in this phase understand that scaling sales is not just about hiring salespeople but about creating systems, processes, and culture. They codify what works and can transfer their knowledge effectively.

I assess founders by their ability to learn to sell, hire the right sales talent, implement effective sales processes, and maintain product integrity while scaling distribution.

Practical tips for founders -> The bottom line is selling is hard but learnable, and it’s even harder when you have to transition from just you selling to now you are assisted by a team selling. The typical trap is hiring sales, not monitoring for success in the first few months, letting too much time to pass before you fire them, spiraling thinking you failed, the revenue stales or you have negative growth and you start thinking of selling instead of thinking you need different people to try and replicate what you did before. Because you sold before, you know that it’s the sales person not the product that’s not working. Almost everyone gets hiring for sales wrong at first, but there are ways to succeed. You’re not broken, it’s hard for everyone. Reach out if you’re struggling with this.

7. Triple Double Phase

Mental Software Requirements:

Attention Allocation: Balanced focus across multiple growth dimensions
Emotional Architecture: Handling increased pressure and expectations
Feedback Processing: Rapidly incorporating learnings from multiple channels

In this phase, founders must scale rapidly across all dimensions – team, product, and revenue. The name refers to achieving substantial growth in multiple metrics simultaneously. The most successful founders here maintain discipline and execution while scaling. They understand how to implement processes without stifling innovation and how to maintain culture through rapid growth.

I evaluate founders by their ability to manage complexity, delegate effectively while maintaining standards, and continue innovating despite organizational pressures.

Practical tips for founders -> AI has introduced new growth/churn behaviors, but the fundamentals of a healthy business have not changed. Scale Venture Partners, has great blogs on metrics for growth, efficiency and observed patterns that are really useful to founders. You don’t have to guess how you’re tracking, you can measure yourself in Scale Studio.

Why It's Never Too Early to Meet Founders

This framework explains why I believe it's never too early to meet founders – even at the chain of thought phase. By understanding a founder's mental software early on, I can:

Identify exceptional talent before traditional signals emerge
Provide targeted support based on where they are in their learning journey
Build authentic relationships based on mutual understanding
Help normalize the challenges they'll face at each phase

Great founders aren't born with perfect mental software; they continuously update and refine it.

By meeting founders early and often, I can observe not just their stated principles but their operational behaviors over time.

Like complex software systems, human minds often have both documented functions (what we say we believe) and actual implementations (how we actually operate), with fascinating discrepancies between them.

My Approach as Your VC Partner

I see my role as more than capital — it's partnership through the psychological journey of building a business. As an investor, I see multiple businesses being built, which is why I can help normalize your experience.

If you're a founder in the early stages of building, or even just starting to think about it, I'd love to connect. I invest at the pre-seed and seed stages, and I enjoy meeting founders long before the world sees what you're building. I don’t need a deck.

And if you're someone interested in the ideas I share here and how I think about investing, I always enjoy connecting with others who believe in backing extraordinary potential early.

Motive Notes

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