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As a second-time startup founder, here are some tactical things I'm going to do differently this time:
1 - Modify how our equity vests

5 year vest (vs 4)
Larger upfront grants
Single trigger acceleration for founding team
10 year exercise period (vs 90 day)
2 - Use a single @AngelList RUV to consolidate all small check investors

I love the idea of people investing $1K-10K in startups & democratizing this asset class

But was annoying to require tons of signatures for everything

This time we'll pool everyone together in one vehicle
3 - Get audited *early*

Will hire real financial leadership as soon it's clear that we have PMF

And make their first task to have our books audited the first calendar year we have real revenue

Will uncover future headaches early & be a big time saver for when it matters
4 - Be somewhat systemic in setting compensation upfront

At some point every business needs to do this & it gets really hard to retroactively fit people into a system designed after the fact

Doesn't have to be mad sophisticated, just some method to the madness
5 - Zero synchronous recurring meetings upfront

I'm sure we will end up adding them, but it's so much harder to subtract any kind of process than add

So we're going to be super careful every time we add any (esp. if it takes away people from actual work)
6 - Ship as little product as possible

Totally messed this up the first time, and personally built and shipped a million features en route to PMF that we had to maintain forever

Goal here is to keep cutting scope repeatedly & have as narrow a product footprint up front
7 - Spend zero money on traditional paid marketing for as long as possible (potentially years)

This strategy will likely vary by industry so not applicable for everyone

But would really want to nail product led growth + every single organic channel before dropping a $ into paid
8 - Have a simple financial model & sanity check cashflow breakeven goals

I'm talking something stupid simple that you don't need a head of finance for

But does the overall math work out for my biz to actually start making money without relying on infinite funding?
9 - Good corporate counsel is 100% worth the $$$, not the place to skimp
10 - Buying a premium domain name upfront

We saw our conversion rate dramatically jump when we rebranded from usefedora.com to teachable.com

If you raise $$, it's totally worth spending $20-50k to get a badass domain that makes everyone take you seriously
11 - The most important tax exemption for startups is QSBS (qualified small business stock)

I'm going to up front make sure:

- our business is eligible for QSBS
- the entire founding team gets equity as early as possible for QSBS
- everyone is educated about QSBS multipliers
12 - Use more contractors (vs employees) for all non-critical business functions

I want to keep our FT team as small as possible

Practically, this means using many more contractors for random tasks

(Corollary - no one who's not a FTE will ever write a line of code in our app)
13 - Do not build subscription billing from scratch

Your SaaS billing needs are not unique and neither are ours

May as well implement what lets you scale to $50M+ in ARR upfront

(This principle is generally applicable to a whole lot more than subscription billing)
14 - Things I will not spend money on until product-market fit:

- An expensive branding agency
- A PR agency
- Conferences or travel
- An expensive office
- Any benefits that are not healthcare (but will have v.good healthcare)

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Gold. Each piece of advice is brilliant. Unless you have been a founder at least once (and suffered through some mistakes), you can’t fully appreciate the depth and pull of each of these points