When I do sales office hours with founders for the first time, the 1st thing I ask is where on the chart below do their customers fall.
From there we can decide on which sales channels may be most appropriate.
A thread below 🧵👇
There are many ways to build a $100M ARR business.
Most startups will not neatly fit into one customer segment bucket, but rather have customers that can segment into various buckets.
But, you still have to choose *a* segment to go after first. The matrix helps. /2
Apr 27, 2022 • 5 tweets • 1 min read
We don't talk enough about our first jobs.
My first job was data entry at a travel agency. I quit after 8 hours.
My second job was two weeks later — the meat department of a grocery store. My parents thought I would quit after a day. I worked there for 5 years and loved it.
My first "business" was a webhosting company I started while in high school. It was ~breakeven and I still remember some of the customers who would message/email me.
Mar 10, 2021 • 10 tweets • 2 min read
It's been almost 10 years since one of my most embarrassing fundraising moments as a founder.
A moment so embarrassing that I couldn’t talk about it for years.
It taught me the difference between raising a Seed round and a Series A, as well as some well needed humility.🧵👇
In 2010, our seed raise was a breeze. We were young, arrogant, and deeply technical — a recipe for an oversubscribed round in 2010.
We confidently handwaved away questions like "how will you get customers?" and spent most of our time building product.
Mar 10, 2020 • 5 tweets • 3 min read
@davidlee@olshansky I 100% agree that the iPhone/mobile had a huge compounding effect that helped many of these businesses as it brought a lot more people online, but I think there were other factors at work then that will also work now:
@davidlee@olshansky - In 2008 startups were starting to become a legitimate alternative to a traditional job. If you found yourself looking for new opportunities, starting a company was one. I think this is 10x as true today as it was in 2008.
Mar 3, 2019 • 9 tweets • 2 min read
I was recently doing office hours with a company that does enterprise sales and that got me thinking once again on the topic of pricing. So, here's a quick THREAD: (1/9)
(2/9) Founders are all too often afraid to charge MORE, and end up underpricing their products. That fear is generally tied to the fear of rejection, and the fear of losing the deal.
