Five years as a startup CTO: How, why, and was it worth it? (2024)

What counts as a startup vs a “regular” business?

• Several definitions offered:
  • A startup is on the “VC treadmill”: raising capital to fund aggressive growth toward a big exit or bust.
  • Another view: it’s a company that hasn’t found product–market fit yet; once it’s profitable and repeatable, it’s just a business.
  • Some argue funding is the key differentiator; others say focus on growth vs stability/revenue is more important than whether VC is involved.
• Question raised about what to call new non-VC, bootstrapped or “lifestyle” businesses; answers included “new business” or “small enterprise.”
• Someone notes that under the growth-centric definition, very large companies like OpenAI/Databricks still qualify as “startups.”

CTO vs CEO: control, equity, and roles

• Strong thread arguing that if you can be a startup CTO, you should often be the founding CEO to control equity and avoid being replaceable once the product is built.
• Counterpoint: CEO work (fundraising, sales, marketing, operations) is a very different skillset; many technical founders underestimate this and sink their companies.
• Domain knowledge and sales skills are repeatedly cited as more critical than technical depth in most verticals, except devtools.
• Some say title (CEO/CTO) matters less than being a founder; others emphasize CEO’s structural power (board alignment, ability to push out cofounders).

Risk, reward, and “was it worth it?”

• Commenters debate whether 5+ years as a startup CTO is “worth it” without a big exit.
• Several highlight survivorship bias: most B2B SaaS never reach meaningful ARR; 500k ARR is not financial freedom and often still stressful.
• Others argue fulfillment, learning, and early-stage autonomy can justify the tradeoff even without a large payday.

Technical vs business work and focus

• Multiple references to the article’s point that not every business problem needs a technical solution; alternatives include support, Zapier-style glue, or explicitly not solving some customer requests.
• Discussion on the need to say “no” to many ideas to focus on what matters now; some CEOs tend to chase any revenue opportunity.

Helios status and unusual go-to-market

• Some assumed the referenced company had died due to dead links; insiders clarified it’s alive but very B2B, relationship- and referrals-driven, historically with little to no web presence.
• This sparks debate: some find a no-website vendor inherently suspicious; others argue a minimal online footprint can reduce noise and bad leads, especially in bank-to-bank sales.

Process, leadership, and QA

• The author describes a lightweight process: epics focused on business value, twice-weekly prioritization, 2-week sprints, engineers breaking work down, strong QA gate, and deliberately ignoring “backlog of good ideas” until the business is ready to act.
• A key leadership theme is “CTO as question-asker,” probing with “why/why now,” impact on security, failure modes, and clarifications rather than issuing top-down orders.
• QA is strongly defended: beyond automation, good QA owns product understanding, test planning, triage, release confidence, and frees leaders from micromanaging testing.