"SideHug" - equip Day 0 startup creators to embrace their side-hustles

[kevan-g]

Our starting point
PostHog wants to equip every developer to build successful products.
We want folks who are starting small.
Yes, we have folks in the Startup program, but we want more of them, and we want them earlier.
We offer good Day 2 tools (for when there are users and a product), but not Day 1 (building the product) and Day 0 (getting started).
What would it be like to equip Day 0 developers for their journey, with the long-term view of really kickstarting their hero's journeys?

Life at Day 0
Before a startup is a startup with a product and users and revenue, it's just: an idea.
An idea trapped in the head of a founder or two.
What gets in the way of a founder actually jumping out of the aeroplane with a parachute?
Do you remember?
(I do.)

Very, very valid excuses and obstacles:

1. I don't have $ money for the software: the AI subscriptions I need, for domain name I want, for a google workspace subscription.
2. I don't have $$ money for the hardware: a good personal computer -- I have a family computer, or a work laptop, but not one for my side-hustle)
3. I'm scared and stuck in my own head (I don't access to advice, coaching, encouragement, support)
4. I have dependents, and if I leap, I won't be able to provide good care for my family in the form of benefits.

The idea
Catalyze more creative entrepreneurial leaps by equipping founders/developers to take the leap into taking their side-hustles more seriously. Emphasis on equip.

Give them what they need. Eliminate every obstacle. Remove any excuse. Make it possible for them to actually get going, even if they are starting small.

We already give Startup enrollees a healthy amount of credits. But Day 0 folks don't need no credits. (Not yet. They will. Once they get started.)

Life at ground-level means people are grinding. Single-income families powered by big dreamers. Folks living not all that far from poverty (today) who don't have investors, capital, connections, a network, net worth, or even good internet. Change the basics, and we change lives, and win fans for life, and tell super crazy compelling stories in the years ahead. If we seriously have "money to burn" and we're ready to be weird, generous and creative, let's offer what can really make a difference.

What's in the package?
Everything that's the opposite of the current Very Valid Obstacles:

1. Money for subscriptions: Their own Brex card with a $300 monthly limit, to cover Google Workspace for two users monthly, access to the software they need (AI subscriptions, API access, etc.)
2. Money for hardware: Let's get them a dedicated laptop and peripherals needed to focus well, instead of having to borrow the family computer or risk moonlighting on work tech
3. Access to coaching & community: Either PostHog leadership time or PostHog community itself can be designed in a way to offer coaching calls, peer advice circles, regular donut-style connects, to get people out of their own heads and into the missing element of community
4. Access to benefits: Let's get them on a group benefits program that offers some basics, similar to what a Chamber of Commerce or early cooperative insurance program would offer. They don't have to be employees to be taken care of. Even some kind of HSA.

(I envision a cost of ~$10,000 CDN / $5,600 GBP / $7000 USD per participant. We could try with a pilot first -- 10 spaces. See where we go.)

Impact

• Builds fans for life. PostHog unsticking the first steps of an entrepreneurial journey will be have more staying power than a sticker on a laptop.
• Creates wildly interesting word-of-mouth stories.
• It could help people really launch interesting companies that go places. You've heard of the PayPal Mafia? This here's the PostHog Effect.

Yes...

• We'd need to have some great minds on the legal, financial, tax implications.
• We'd need to be think through our principles on selection and qualification / randomness, etc.

Naming and branding?
I like SideHug.
PostHog's got your back side.
Don't quit your side-hustle.
(Powered by PostHog.)

A few things we could do to start:

• Gauge our willingness to do this (leadership gut check)
• Initial financial model on the costs
• Do a user survey with recent founders to ask THEM: what were the barriers to Day 0 entrepreneurship? What would have made a real difference?
• Slap Kevan and say "next idea, please"

[joethreepwood]

Quick feedback on this is that I think this will work closer to the brand if we come at it from a point of opinion, rather than wealth. By which I mean: instead of just giving them $300 on a Brex credit because we can, we identify the tools we think they need and built a relationship with those companies to offer resources directly? We then also unlock the opportunity to co-market with those teams and aren't just throwing money at a problem without direction.

I'd also stop short of just buying PCs for people. That'll be too pricey too fast and have minimum value for them, I think (if you don't even have a PC are you really launching a new startup?).

The other angles and the broad direction seem great though!

[kevan-g]

(A little note about some noise/alerts here: I was using GitHub issues to take notes during my onboarding week. I had thought our work-in-public vibe meant i should also track my own personal notes/jots here (whether or not I needed collaboration input). Now I see this only adds clutter and adds noise. I'm going to close a bunch of those issues, but that's not me saying they are "done" or "completed," just me hitting reset on how I track things. Apologize in advance for these annoying notifications.)