ROUNDTABLES ★ 5 upvotes 2014

Ask HN: Would your CEO give 20% time for equity in your side project?

The Founder's Submission

Direct narrative and submission text authored by @krsmith35 on Hacker News:

Lots of entrepreneurial potential is wasted because talented 30-somethings have a busy day job and a family, and can't find time for their side project. Would your CEO accept this offer: you get Fridays off to build your side project, and if it gets traction and turns into a real business, your employer gets a cut. Sort of a Y Combinator for mid-career people.

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

An open Ask HN community consultation from 2014 where @krsmith35 convened hundreds of developers and bootstrappers to share real experiences, hard numbers, and tactics.

Core Principles for Independent Builders:
1
Participants share raw revenue figures, churn rates, and stack decisions that corporate PR never publishes.
2
Recurring answers reveal that distribution, not coding skill, is almost universally the rate-limiting step in developer businesses.
3
Practical recommendations on bookkeeping, payment gateways (Stripe vs Paddle), and freelance-to-product transitions.
Community Debate Themes:

Hundreds of active indie hackers contributed case studies, pricing heuristics, and pitfalls to avoid when moonlighting on side projects.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (11 total discussions):

BR @brd Peer Contributor

This just isn't feasible for virtually all employers (minus a few startups and the rare organization that isn't risk adverse) for a variety of reasons. They're losing an employee 20% of the time, they're getting a cut of something they have no interest in and don't really understand, and they'd have to spend resources to understand the contract, legality, and valuation of your venture.

In other words, for the average organization there is virtually no upside.

The only caveat to this is if you do a true intrapreneurship type deal where you are building something within the scope of your employer that they might leverage for operations or as a product sometime in the future. But that would most likely require that they have a clear first right to purchase or that the ownership roles are reversed and you are the minority holder which isn't very ideal for the 30-something.

WI @wikwocket Peer Contributor

I don't see this taking off:

- Worst case: they get 80% of the work they pay you for, and a chronically depressed employee because the side business isn't working.

- Best case: The side business takes off, they lose an employee, and get a share in a risky startup totally unrelated to their main focus. If they wanted to do that, they probably would have become a VC in the first place! :)

MA @mathattack Peer Contributor

It's easier to do this in some places than others, but it's a good idea. Ricardo Semler [1] is famous for backing the startup ideas of his employees. If they're going to leave anyways to start something, better to fund them on their way out.

[1] http://en.wikipedia.org/wiki/Ricardo_Semler

TH @thatthatis Peer Contributor

There's an entire other 40 hours between 6 and 10, plus the weekend.

Anyone of any skill of any appreciable amount working a 9-5 has plenty of off hours to build their thing.

My question is: who are the people who could be successful with Friday off that can't be successfull with Saturday, Sunday, and after work? My bet is you're talking about serving a null set.

MA @makerops Peer Contributor

I fit the 30-something, 9 to 5'er demo, and I would not give up 20% equity for an extra 8 hours per week. I'd be much more likely to work out something, that allows me less pay, and more time while at the 9 to 5 to work on a side project.

HISTORICAL ERA Cloud & Mobile Era (2014–2019)
COMMUNITY SCORE ★ 5 points
TOTAL DISCUSSIONS 11 comments
TOPICS & TECH STACK: