How to build a vivid vision and scale a company from startup to 100 people

Executive overview

Most entrepreneurs scale by working harder rather than smarter — repeating the same habits, never training their managers, and failing to articulate where they are going. Cameron Herold argues the fix starts before you hire anyone: write a vivid vision, a four-page description of your company three years from now, and share it so the right people self-select in.

The same logic applies at every stage. From solo founder to 100-person company, the bottleneck shifts from revenue to people to management skills — and ignoring that shift is why most companies stall.

The core bottleneck at every growth stage is the skills gap between what your managers are asked to do and what they have been trained to do.

Following the path of least resistance as a founder

• Stop being the fly at the window. If there is friction, find the open door — the shortcut someone else has already mapped.
• Millions of companies have solved what you are solving. Find their playbook and use it.
• Work on the things that give you energy; delegate or outsource everything else as fast as possible.
• Choose a business area you genuinely like — operating in one you don't will drain you even if it grows.
• In the early days, prioritise revenue over perfect product, perfect funnel, or perfect email. Momentum creates momentum.

The ones and threes: how the CEO job changes at each stage

• Solo to 3 people: focus entirely on highest-ROI revenue activities; hire generalists who can get things done quickly, not experts.
• 3 to 10 people: delegate projects, keep tasks that energise you, build out better systems once you have a small team behind you.
• 10 to 30 people: you stop managing everyone directly; grow your first managers' skills and confidence in parallel — skills ladder and confidence ladder together.
• 30 to 100 people: your management team runs the business; your job is growing their capability through structured training (coaching, situational leadership, delegation, meeting management).
• 100+ people: hire experienced leaders from outside; manage politics and silos; protect A and B players.

The vivid vision as a hiring and alignment tool

• A vivid vision is a four-to-five page document describing your company as it will look in three years — written as if you are walking through it.
• Write it without worrying about how you will get there. Describe what you see, not the plan.
• Share it with everyone. People who love it will want to join. People who don't will self-select out.
• If you cannot see the destination clearly, your team cannot build it for you.
• Pair the vivid vision with a job posting polished by a copywriter. A great posting should repel 50% of readers — the ones you don't want.
• Treat hiring like client acquisition: the job description is your copy, and you are attracting a critical asset.

Why most companies stall between 30 and 100 people

• Managers are asked to coach, interview, run meetings, and handle conflict — and almost none of them have been trained to do any of it.
• Sending someone into management without training is like sending a child to play cricket for the first time without showing them how to hold a bat.
• Most companies train on the what (social media, landing pages, tools). The how — coaching, situational leadership, time management — is what gets you from 30 to 100.
• "20 years of experience" is often five years of experience repeated four times. Without deliberate skill-building, people plateau.
• The fix: structured manager training that grows both skills and confidence simultaneously.

Scaling from 50 to 100 people: culture and people decisions

• Obsess over core values. Anyone who does not live them must go, regardless of their results.
• A values mismatch is a cancerous tumour — the longer it stays, the more damage it does to A and B players.
• When letting someone go, use one of two statements: "It's not working on results" or "It's not a culture fit." Repeat calmly; do not get drawn into debate.
• Give your time to A and B players, not C players. A players are racehorses, B players are workhorses, C players go to the glue factory.
• Politics and title-jockeying emerge around 100 people. Spot it early by watching energy and how people approach problems.

CEO attributes worth building deliberately

• Entrepreneur stage: minimum viable everything; attract and grow people; sell the vision relentlessly; keep growing your own skills.
• CEO stage: communication, strategy, and network. Stop asking how; start asking who.
• As a CEO you have a moral obligation — not just an opportunity — to build a company that gives employees a better life. Doing that also happens to make you more money.

On fear, failure, and mental state

• A little fear keeps you focused; too much paralyses you and radiates into your team.
• Be worried with your mentor, coach, or mastermind group. Walk into the business as the chief energising officer — optimistic, unbridled, "we'll figure it out."
• Fail forward: try something, move on, try something else. Do not repeat the same mistake. Copy what already works.
• Momentum matters more than perfection. Quick beats perfect at every early stage.

What Cameron would do differently

• Release ego and find quiet confidence earlier. Cockiness at 21 was a liability.
• Delegate far faster. Radical self-reliance felt like hard work but was mostly working below his own pay grade.
• Surround yourself with coaches and mastermind communities from the start — College Pro Painters, EO, YPO, Genius Network, Strategic Coach all contributed to his development.