From maker to entrepreneur: Balsamiq's 7-step journey

Executive overview

Most founders start as makers, but success forces a series of job changes they never signed up for. Each transition — from maker to manager to CEO to business owner — requires discarding old instincts and learning an entirely new role.

The core mistake is treating the company as a product to be invented from scratch. Proven systems exist for org structure, values, salaries, and planning. Adopting and configuring them beats reinventing everything.

Your job as CEO is to provide clarity — it's the one thing you can't delegate.

The 7 stages of the founder journey

1. Maker — builds the product
2. Successful maker — product gets traction, transition required
3. Founder — incorporates, deals with lawyers and accountants
4. Manager — hires first employee, loses best maker, gains a shitty manager
5. CEO — delegates all making, figures out what a CEO actually does
6. Business owner — builds leadership team, steps back from day-to-day
7. Entrepreneur — sells or starts another business; the company is a thing separate from you

Not everyone completes all seven. Some exit at step four or five; co-founders often split the journey.

Your business is a human-powered system, not a product

• Treating the company as "your second product" is dangerous — it leads to reinventing standard HR policies from scratch.
• A business is more like democracy: a system of people working together correctly.
• Innovate on the product; adopt proven systems for how the company runs.
• You do choose: culture (sync vs async, remote vs office, fast vs laid-back) and the problem you want to solve.
• The problem you choose dictates your company size and playbook — a food truck and "eradicate malaria" require completely different structures.

Adopt existing systems rather than building your own

• EOS (Entrepreneurial Operating System) is popular at Balsamiq's size — based on five books, with consultants, YouTube videos, and ChatGPT fluent in it.
• Other options: Lean Startup, Holacracy, Atlassian Plays.
• Choosing an existing system is like choosing Tailwind over bare-bones CSS: proven, evolving, and well-supported.
• ChatGPT is fluent in these systems — create an EOS expert by feeding it the books.

Structure and org design

• A flat org chart is a myth: leaders emerge anyway, but without titles they aren't accountable.
• Add an org chart (EOS calls it an accountability chart) as soon as you have two or three people.
• Give employees real job titles — they need them for conferences and career clarity.
• Buy job titles and salary data from a provider like ERI (6,000 roles with level definitions and hard-skill breakdowns).
• Soft-skill frameworks can be generated with AI; keep them in a table with level 1–3 definitions.

Vision, values, and strategy

• Values are the north star. Vision is a 10-year snapshot. Mission provides milestones. Strategy is the path to the first goal. Roadmap is quarterly projects.
• Two questions to find your vision: why does the organisation exist, and what can you do better than anyone else?
• Company values have an expiration date — set it to three or four years and communicate that upfront.
• Values must be actionable, not inspirational: "be efficient" works, "be a good teammate" is too vague.
• Use the EOS People Analyzer: for each value, each person is rated most of the time / sometimes / rarely — a minus means fix it or exit.

Salaries and skills maps

• Buy salary data globally (ERI and similar providers cover 6,000 jobs worldwide).
• Build a formula: weight by role split, experience level, and a Balsamiq premium for historically underpaid roles (+10%) and a reduction for overpaid ones (-10%).
• Update annually for inflation.
• Skills maps: team members self-rate 1–5 per skill; overlay the whole team to spot gaps at a glance.

Planning and roadmaps

• Strategy chart: Y axis = focus/effort, rows = collections of projects, high priority at the top with a deliberate gap below it.
• Leave room for a "delighter" every quarter; use arrows to show future-planned work so you can say no with a date.
• Quarterly roadmap: categorise work by type (QA batches, big features, small features, process improvements) and assign capacity limits per category.
• Pick pages: a running buffer page for ideas that arrive mid-quarter. Ideas go there, not into the current sprint. Review at quarter-end during planning.

Discovery and product development

• Run a double diamond process: desk research, competitive research, stakeholder interviews, user research.
• Write insights as bullets, then convert to solution statements before designing.
• Some solutions are not code — tutorials, process changes, videos.
• Split development into prototype (quick and dirty, throwaway 10%) and delivery phases; faster iteration overall.
• Quantitative data is dangerous early-stage — not statistically significant. Use the explore → expand → extract framework: qualitative at the start, data later.

Collaboration tools

• Human User Guide (HUG): one page per person — working hours, communication preferences, how to give feedback. Takes 10 minutes, saves many.
• Team agreements: short, actionable contracts the team writes together on how to collaborate. Review quarterly; update when tensions arise.
• Meeting cadences and agendas: EOS provides templates — don't reinvent them.

Thinking like an entrepreneur

• Refusing to sell means you're not an entrepreneur — you've fused your identity with your company.
• Running the business as if it could be sold at any time forces good profitability, good delegation, and a strong leadership team.
• Key reads: Finish Big and Rob and Sherry Walling's Exit Strategy.