It is OK, right before you take a check from an investor (big or small), to ask

“What happens if we lose it all?”

It might even be wise to ask
There’s actually no right or wrong answer

A truly successful VC will say, “It won’t make a difference”, because it won’t, across a strong portfolio

A nervous angel or someone writing first large check — it could be a career limiting move to lose the money they just gave you
Somone who the loss won’t impact at all, likely won’t really be >that< engaged until you are really doing well. Sometimes, decacorn well.

Someone who has more to prove will show up more. They will help more. They will hustle more. And they may also freak out more.
The bottom line is it’s good to ask the question of every investor, it’s part of founder due diligence on their investors

And just listen

You’ll hear in the answers what things will be like when bumps come
A bit more here:

saastr.com/dont-worry-abo…

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More from @jasonlk

Jan 26
Most of the causes of deceleration on the way from $2m-$100m ARR is getting the timing on your management teams wrong

Too slow to a 1.0 team, you stall out from $5m-$15m ARR

Too slow to a 2.0 team, you stall out from $15m-$30m ARR

But it's not that simple ...
Just as risky is "topping" a great 1.0 VP team with inferior 2.0 VPs

The top 1.0's just leave, with all their domain expertise and learnings

You have to keep all the great members of your 1.0 mgmt team

Ideally, forever
But get this sequencing right, and other issues fade away

A great VPP/CPO and VPS/CRO figure out where to take the customers and product

A great VPE figures out how to scale you

A great VPM finds new sources of leads to keep the funnel filled
Read 4 tweets
Jan 22
Demand Gen is #1 priority in marketing until you have a dominant brand and high market share

Then, Brand Marketing is more important

After that, Demand Gen becomes just a function, a department

But listen, that like almost never happens before $30m ARR
This is why, when you go a large tech company, “Demand Gen” is often run by mid-level marketers

After all, everyone has already heard of Salesforce, Adobe, really even Canva, Datadog, etc.

Brand marketing ensures you >stay< in every deal

Vs

Demand gen >gets< you into deals
So when you hire a VPM that never worked < $30m ARR, they just won’t know

They won’t really know what Demand Gen is

They may say they did, or had someone that worked under them with title

But brand got them into every deal

They never succeed in getting you >into< deals

Never
Read 6 tweets
Jan 14
So every day there are more and more massive funding rounds

But where does all that money >come from<?

1/ From "Limited Partners", the ones that give VCs $ to invest

And they had an incredible year

Top endowments and LPs saw a jaw-dropping 62% (!) returns from VC + PE in 2021
2/ Top LPs (endowments, universities, family offices, etc) did even better than that

Wesleyan's endowment for example grew 54% overall last year, and 95% from venture and private equity (!!)

Woah

And many / most are (re-)investing even more into VC + PE after those gains
3/ As you can, these huge gains (even though many are on paper), so swell endowments that for now, even with some market tumult, there's more and more investment dollars to go into venture and PE

Look how much Wesleyan's endowment grew in 2021, and it's a relatively small one:
Read 7 tweets
Jan 9
So Braze is a great SaaS IPO you make have missed

It's a next-generation marketing platform built mobile-first, with a focus on bigger deals and enterprise

It took off almost immediately

It's at $260m in ARR, growing 63% YoY

5 Interesting Learnings: 🔽🔽🔽🔽🔽
#1. $500k+ deals make up half their revenue, and $1m deals 37%

Big deals fuel the growth at Braze. Still, Braze isn’t overly concentrated, with no customer being over 5% of their revenue. A classic “going more and more upmarket” enterprise playbook.
#2. 126% NRR Overall, and 135% in their $500k+ customers.

What you’d expect, and it’s helpful to see this segmented. The Really Big Customers have 135% NRR. You should aim for the same with similar-sized B2B customers.
Read 10 tweets
Jan 4
So Justworks is going public at a $1B run rate (!)

Or is it $100m ARR?

It shows the complexity of many payroll and SaaS HR apps: Image
The "SaaS" business is at a $110m ARR run rate with OK gross margins of 60%

But the $1B+ of benefits and insurance "ARR" it also has only have a 5% gross margin

A reminder how much revenue quality matters
We see a lot of fintech and payroll / HR apps valued at SaaS-like multiples in private rounds on >all< their revenue, not just the "SaaS" part

Justworks IPO'ing at $2B valuation is 20x SaaS ARR -- pretty reasonable for a strong SaaS company

But it's just 2x total revenue
Read 4 tweets
Jan 1
THANK YOU to everyone for making 2021 a big year for SaaSt:

8 STATS:

#1. Largest IRL tech event in Bay Area.

It cost an extra $2m and took 2 extra weeks to build out, but moving SaaStr Annual outdoors into a festival-style event rocked.

Thx to 5,000+ that came!! Image
#2. 5 Major Digital Events.

With 100,000 total digital attendees, we had the best of the best join SaaStr University, SaaStr Build, SaaStr Money, SaaStr Scale, and Annual Digital Image
#3. SaaStr Podcast Grew Streams 170% and Listeners 149%

We rebooted the podcast a bit per your requests, and thanks for driving it up! Image
Read 10 tweets

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