Summary

• Unlike what sometimes feels like a dark art of finding PMF, Founders can prepare for organisational inflection points. The danger is actually in accumulating ‘People Debt’ that’s largely avoidable and harder to unpick afterwards. 

• I reunited with Rachel Turner, Co-Founder of the VC Talent Lab and author of The Founder's Survival Guide to chat about how founders can prepare ahead for inflection points as their company scales. Our whole conversation is here (link).
  
• This first instalment focuses on the challenges that arise when your company reaches about 50 people

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In the Iliad, the Oracle predicts that Achilles will die young but achieve eternal glory. His mother tries to prevent this by hiding him, hoping to change his fate. Ironically, this directly leads to the prophecy’s fulfilment. This pattern repeats across all mythology: heroes try to escape their fate, only to end up causing the very outcome they were trying to avoid. 

What’s my point? Every startup’s journey is different, but especially when it comes to the human factors, there are themes that reoccur again and again. Most people don’t set off to be a bad boss, but even the best intentions can unravel under pressure. That’s why it’s crucial for you to prepare for the inevitable challenges that lie ahead. Embracing foresight and preparing for future team challenges is far more effective than attempting to ignore or evade them. 

The difference between successful and unsuccessful companies lies in their resilience in overcoming inflection points. Recognizing that the next inflection point is always just around the corner is crucial. The mean time to recover after hitting a wall at an inflection point determines a company's velocity and ultimate success.

Building a team and infrastructure around solving these inflection points is key. 

- Christian Owens, Co-Founder of Paddle 

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Rachel calls this first leg of the founder journey the Brave Warrior Phase. To get here, your strengths and superpowers have helped you unlock capital and customers. Through sheer will and brute force, you have willed your idea into existence and built an entire team around you. But what got you here, won’t get you there. Those early successes will almost certainly lull you into a false sense of security that you should double down on what’s tried and true when challenges begin to mount. 

Inflection points: Your superpowers at one stage are the kryptonite of the next

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The first major trial for founders is when your team pushes past 20 people, or when ‘management’ activities begin to take up more time. 

Why? 

It’s usually when the first real management layer is created (and a signal for increasing velocity of headcount growth), which happens to coincide with the science-backed number for the number of friendships people can have. Once you exceed this number, it starts to feel less like a tight-knit band of pirates and more like a business. 

It’s important you recognise what it feels like when the growing pains begin to set in. The challenge here will be to prepare and practise self-awareness that can help you from reacting to scenarios with a threat response or reverting to old habits. 

Here are some things Rachel and her team at VC Talent Lab encourage founders to remember at this part of the journey when you begin feeling the growing pains of leadership: 

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1. Don’t treat people the way you’d like to be treated. 

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One major bias trap founders often fall into is assuming that others need what you need, and that you should treat people the way you want to be treated. This is a critical mistake.

Remember that you are the founder. Everyone else is here to do a job. Yes, entrepreneurial spirit is much higher among startup operators, but ultimately if they’ve taken a job with you rather than start their own business, it's because they want a job. They want clarity and certainty more than they want freedom. 

Don't treat people the way you want to be treated. Treat the people the way they want to be treated.

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2. Over index on clarity and communication

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People need to hear things at least six or seven times in different ways for it to stick. Channel more Considered Architect as soon as you feel the need to build up scalability, which in practice, means emphasising over-communication and clarity. This is going to feel unnecessary, but believe us, it’s not: you may think you've said something clearly, but say it again three or four, five more times anyway. 

The challenge is resisting the urge to double down on what’s comfortable when what’s needed is a change in tack.

You've used those muscles again, and again and again. And it's like thinking about a body, if you've only used your right arm, your left arm starts to get quite weak. The temptation you'll have is to always use the right arm for everything, because you know how to use it. And it's easiest. But when you get to the point where the business now requires you to delegate consistently, to create clarity, to create the environment where your people get what they need from you,

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3. Delegate but don’t abdicate

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As more ‘management’ activities like facilitating meetings and performance reviews arise, the temptation will be to hire someone to oversee it for you instead. And you should be attracting people to the company that can do the work better than you. But what can happen is total abdication of responsibilities and an eventual disconnect - Founders will bring in a COO or CFO, never speak to them, never show up at any of the meetings never follow any of the protocols that the CFO has set, reverse decisions when staff come to them rather than go to the CFO and then wonder why this shiny new hire isn’t performing the way they’d hoped. 

What you need to do here is think about minimally viable ‘architecting energy’. You don’t need to go out and read every management book ever written, but you do need to stay engaged rather than revert to your comfort zone of building or selling. 

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The Double-Edged Sword of ‘Brave Warrior Energy’

To summarise - forewarned is forearmed. What got you here might actually derail you as you scale. The temptation to double down on your strengths can be a trap. Instead, be thoughtful and consistent. Communicate clearly, reinforce key messages, and adapt your approach to guide your team through growth challenges effectively.

In the next section, we’re going to be talking about the inflection points related to the Build phase of startups.