Nurturing Companies

April 2017. One of our startups (seven months old, $50,000 invested) was stalling. The product worked. Customers liked it. But sales weren’t accelerating. The founders were working hard, but something wasn’t clicking.

I sat down with the CEO and asked: “What phase are you in right now?”

She looked confused. “What do you mean, phase?”

“Are you still figuring out product-market fit? Are you scaling something that’s working? Are you pivoting? Where are you in the journey?”

Long pause. “I… don’t know. We’re just trying to get more customers.”

That’s when I realized the problem. They didn’t know what game they were playing, so they couldn’t know if they were winning.

A startup at the “find product-market fit” phase needs totally different management than a startup at the “scale what’s working” phase. If you treat an early exploration like a scaling operation, you’ll optimize too early and miss the real opportunity. If you treat a proven concept like an exploration, you’ll dither while competitors execute.

The builder’s job isn’t just to provide resources: it’s to correctly diagnose which phase each startup is in and apply the right kind of support for that phase. Get it wrong, and you can kill a company with bad advice. Get it right, and you accelerate their progress dramatically.

Over the years, I’ve identified four distinct phases that startups move through, and learned what each phase needs from the builder. This isn’t academic theory: it’s a survival map I wish I’d had when we started.

The Four Phases of Startup Development

Phase 1: Discovery (Months 0-6)

What’s happening: The team is exploring. They have a hypothesis about a problem and a solution, but they don’t really know if either is correct. Every customer conversation is an experiment. Every feature is a guess.

What they need from the builder:

Permission to be uncertain: Don’t expect a polished pitch or detailed roadmap. They should be learning, not executing.
Customer access: Introductions to potential users. The faster they can get to 20-30 real conversations, the faster they’ll find the signal.
Protection from scaling too early: They’ll want to build the “full product.” Stop them. MVP only.
Weekly check-ins: Short, frequent touchpoints to hear what they’re learning.

Red flags in this phase:

Building features without talking to customers
Spending money on marketing before product-market fit
Getting defensive when we question their assumptions

Success looks like: They start saying “customers keep asking for X” instead of “we think customers want X.”

Phase 2: Validation (Months 6-12)

What’s happening: They’ve found something. Multiple customers have said yes. The pattern is emerging. Now they need to prove it wasn’t a fluke: can they repeat the success systematically?

What they need from the builder:

Process discipline: Help them document what’s working. Why did that customer buy? What was the sales process? How long did it take?
Early customer success support: They’re probably terrible at onboarding and support. We can help standardize it.
Financial modeling: They need to understand unit economics. What does it cost to acquire a customer? What’s the lifetime value?
Hiring guidance: They’ll need their first employees soon. Help them hire right.

Red flags in this phase:

Celebrating five customers like they’re at scale (you’re not)
Inconsistent results (customer 3 loved it, customer 5 hated it; you haven’t validated yet)
Premature team expansion

Success looks like: They can tell you exactly why customers buy, how long sales take, and what the next ten customers will probably look like.

###Phase 3: Scaling (Months 12-24)

What’s happening: They’ve proven it works. Now they’re stepping on the gas. Hiring, marketing spend, feature expansion. This is exciting and terrifying.

What they need from the builder:

Operational infrastructure: HR processes, financial controls, customer success systems. The scrappy startup approach breaks at scale.
Strategic guidance: They’re making big bets now. Wrong hires, wrong features, wrong markets can blow up the company.
Cash flow management: Growth eats cash. They need tight treasury discipline and probably more funding.
Monthly board meetings: The stakes are higher. We need more structured oversight.

Red flags in this phase:

Growing expenses faster than revenue
Losing the culture that made them successful
The founders getting overwhelmed by management (they’re first-time managers managing managers)

Success looks like: Month-over-month growth in customers and revenue, improving unit economics, the team growing but still aligned.

Phase 4: Maturity (24+ months)

What’s happening: They’re a real company now. Product-market fit is solid. Team is 10+ people. The challenges shift from “will this work?” to “how do we sustain and expand this?”

What they need from the builder:

Less, but higher quality: They don’t need weekly hand-holding. They need experienced advisors for specific challenges.
Network access for partnerships and exits: Introductions to strategic partners, acquisition conversations, larger investment rounds.
Permission to run their own company: The builder’s job is to support, not control. If they’ve gotten here, they’ve earned autonomy.

Red flags in this phase:

Stagnation: they’re comfortable but not growing
Founder burnout: they’ve been sprinting for two years
The builder holding on too tight

Success looks like: They call the builder when they need it, not because the builder is checking in. They’re making good decisions independently.

The Art of Ripening Control

One of the hardest lessons I’ve learned is when to tighten control and when to loosen it.

In early 2018, we had two startups that were both struggling. My instinct was to increase oversight on both: more check-ins, more guidance, more hands-on involvement.

Startup A was in Phase 1 (Discovery) and the founders were experienced. They just needed time to find product-market fit. My increased oversight slowed them down. They started optimizing for my approval instead of customer feedback. It took me three months to realize I was the problem. When I backed off, they found their rhythm and closed their first three customers in six weeks.

Startup B was in Phase 3 (Scaling) and the founders were first-timers. They were growing, but financial controls were a mess. They were hiring too fast, burning cash dangerously. My increased oversight saved them. We implemented weekly financial reviews, hiring approval process, and operational dashboards. They hated it at first (felt like micromanagement). But it prevented them from running out of money at the worst possible time.

Same instinct (tighten control), opposite results. The difference was context.

The rule I’ve developed: Early-stage startups with experienced founders need space and optionality. Later-stage startups with inexperienced founders need structure and process. Get that wrong either way, and you harm more than you help.

Mentor Teams: The Brain Trust

Solo entrepreneurs are gambling with their own limited knowledge. Builder entrepreneurs have access to collective wisdom, if we structure it right.

We assign every startup a “brain trust” of 3-4 people:

The lead builder partner (usually me): Strategic guidance, fundraising, conflict resolution
A domain expert: Someone who knows the industry/technology deeply
An operational mentor: Someone who’s scaled a company and knows the practical challenges
A peer founder: Another entrepreneur in the portfolio who’s 6-12 months ahead

This isn’t a formal board (we have that separately). It’s an informal advisory group that the founders can tap for specific questions.

The key is making it low-friction. Founders won’t use mentors if every conversation requires a formal meeting. We do:

Monthly group calls (30 min, whole brain trust, review progress)
On-demand pings (Slack/email, quick questions anytime)
Deep dives when needed (Specific problem? Schedule a focused session with the right mentor)

The Mentor Mistake I Made

In 2016, I thought being a good mentor meant being available constantly. One founder was Slacking me 5-6 times a day with questions. I answered every one, usually within an hour.

I thought I was being helpful. I was actually making him dependent.

Six months in, he couldn’t make a decision without checking with me first. “Should I hire this person?” “Should I price it at $50 or $60?” “Should I add this feature?”

These weren’t strategic questions requiring my expertise. These were operating decisions he should have been making himself. By being too available, I’d trained him to outsource his thinking.

I had to have an uncomfortable conversation: “I’m going to respond slower to tactical questions. I’m here for the hard strategic stuff, but day-to-day decisions are your job.”

He was frustrated at first. Within a month, his decision-making speed doubled. Within three months, he was confidently making calls I wouldn’t have thought of. My pulling back made him better.

Now I’m more selective about when to engage. Strategic inflection points, conflict resolution, major hiring, fundraising: I’m all in. Daily tactical stuff, they figure it out or ask their peers.

Conflict Resolution: The Win-Win-Win

Conflicts are inevitable. Co-founders disagree. Entrepreneurs and builders disagree. The question isn’t if conflict will happen: it’s how you resolve it.

Most conflict resolution advice focuses on finding “win-win”: a solution where both parties feel like they got something. That’s fine for business negotiations. It’s insufficient for venture building.

In a venture builder, there are three parties to every conflict:

The entrepreneur(s)
The builder
The startup itself

Traditional win-win thinks about #1 and #2. But the startup (the actual company trying to succeed in the market) has its own interests that sometimes conflict with what the entrepreneur wants or what the builder wants.

The Salary Conflict

July 2019. One of our CEOs wanted to raise his salary from $2,000/month to $4,000/month. He’d been living lean for 18 months and was burned out.

His argument: “I’m barely surviving. I need a livable wage.”

My instinct: “We can’t afford to double your burn rate. You need to stay lean.”

Classic founder-builder conflict. We could argue forever about what’s “fair.”

Instead, I asked: “What’s best for the startup?”

We pulled up the numbers. The company had $40,000 in the bank, was burning $6,000/month, had three months of runway, and was six weeks from closing a $25,000 deal that would extend runway to eight months.

If we doubled his salary, burn would go to $8,000/month. Runway would drop to five months. We’d hit zero before the deal closed.

The startup couldn’t afford the salary increase. Not because I was being tight with money, not because he didn’t deserve it, but because the mathematics of the company’s survival made it impossible.

Once we framed it that way, the conflict dissolved. It wasn’t “Taig vs. CEO.” It was both of us looking at the startup’s reality together.

We found a different solution: He increased his salary to $2,500 (manageable for the company’s budget), and we agreed to revisit after the deal closed. If revenue came through, we’d bump it to $4,000.

Win-win-win: He got some relief. I stayed within financial constraints. The startup survived.

The Principle

When you’re stuck in a conflict, stop debating what each party wants and ask: What does the startup need to succeed?

Both the entrepreneur and the builder are supposed to be in service of the company’s success. If we agree on that, then we can look at the situation objectively and find the answer together.

Sometimes the answer favors the entrepreneur’s position. Sometimes it favors the builder’s. Sometimes it requires both sides to compromise. But by making the startup’s interests the tiebreaker, you can’t have prolonged partisan conflicts.

This works for:

Co-founder equity disputes (What split makes the company most likely to succeed?)
Hiring decisions (Does the company need this person now or can it wait?)
Feature prioritization (Which features most directly drive revenue/retention?)
Fundraising timing (Is the company ready to raise, or would raising now harm valuation?)

Put the startup first, and most conflicts resolve themselves.

The Pivot Conversation

I’ve written about pivoting as a commandment for entrepreneurs. But as the builder, how do you know when to push for a pivot vs. encourage persistence?

This is the hardest judgment call in venture building. Push too early, and you kill something that just needed more time. Push too late, and you waste months on a dead end.

I don’t have a perfect formula, but I have a checklist:

Consider pushing for a pivot when:

The team has done genuine customer discovery (30+ conversations) and the feedback is consistently negative or apathetic
Sales cycles are 3x longer than industry standard with no clear reason why
Early customers aren’t converting to active users, suggesting no real value delivery
The founder is articulating the problem more clearly than customers are, meaning you’re solving a problem people don’t actually have
Every conversation reveals a different, more urgent problem that your current solution doesn’t address

Resist pushing for a pivot when:

The team hasn’t given it enough time (less than 6 months of active customer engagement)
There are positive signals mixed with negative ones (this is normal early-stage noise)
The problem is execution, not concept (bad pitch, bad positioning, bad product: these are fixable)
The founder has deeper domain insight than you and can explain why your concerns are wrong

The gym startup I mentioned in The 5 Commandments? That was a clear pivot case. Eight months of effort, dozens of sales conversations, single-digit success rate, and every gym owner was telling us “this solves a problem I don’t have, but I do have this other problem…”

Contrast that with another startup that spent five months with zero sales, but customers they talked to were genuinely excited, just not ready to buy yet (timing issue, not value issue). We didn’t push for a pivot. We helped them find earlier-stage customers who were ready. They closed their first deals in month six and have been growing steadily since.

Pivoting should be a data-driven decision, not a frustration-driven one. Gather the evidence, look at it honestly with the founder, and make the call together.

Nurturing a portfolio of companies is less like gardening (passive, predictable) and more like coaching a sports team (active, adaptive, contextual). Every company is different, every phase requires different support, and your job is to read the situation and provide what’s needed.

Sometimes that’s hands-on guidance. Sometimes it’s hands-off space. Sometimes it’s tough love. Sometimes it’s patient encouragement.

The builders who get this wrong are either too hands-off (providing capital but no guidance) or too hands-on (micromanaging grown adults). The builders who get it right are calibrated: present when needed, absent when not, always in service of the startup’s success rather than their own ego or the entrepreneur’s comfort.

It’s messy work. It’s relationship work. It’s the most human part of venture building. And when you get it right, you get to watch an idea become a real business, and know you played a part in that transformation.