At Udemy, we were 3 first-time entrepreneurs trying to raise seed capital. We made every mistake in the book.

We got 200+ no’s and wasted 12 months fundraising.

We eventually pulled through, just barely. 😅

This thread shares our mistakes as lessons for founders.

**Read On**
We built an impressive product, but we were nobodies.

We thought: we need money to build our vision, so let’s go talk to some investors.


Nobody gave a fuck that we needed money. We needed to prove we deserved their money.
We met some associates and intermediaries who might introduce us to investors.

Few decision-makers wanted to meet with us.

We should’ve stopped there.

If getting meetings is hard, it will take you forever to raise.

Instead, spend your time building product + getting traction.
I was frustrated with investors: treated them as adversaries who asked dumb questions. My derision turned them off.

Learn to understand and appreciate investors. Follow them on Twitter, listen to podcasts from @HarryStebbings or @eriktorenberg.

An investor's job isn't easy.
They kiss a ton of frogs just to find one deal that may make them money 10 years from now.

They only win if you become a billion dollar company.

Don’t kid yourself - if you aren’t the right fit, bootstrap.

Risk-adjusted, bootstrapping can make you happier and more successful.
When pitching, we were too in the weeds - talking about next quarter or next year.

Investors don’t give a shit about next year. They care about the next decade.

Paint a picture of 10 years in future: how will the world be different and how will you build a $1B+ business?
We finally got some meetings. We had 50 meetings in 3 weeks.

Everyone said no except one Turkish billionaire.

Don’t trust Turkish billionaires. Don’t trust any investors who are outside of the Valley ecosystem.

The billionaire ghosted us.
After that many no’s, we accepted defeat and regrouped.

We had made a huge mistake: we didn’t launch! Investors could smell our launch anxiety and didn’t invest because there was no traction or urgency.

Show the investors you’ve got chutzpah. Press the button.

We built “Silicon Valley hype” with our launch - TechCrunch, Mashable and ReadWriteWeb covered it (this was 2010!).

We were on top of the world, and sent some follow-ups to investors.

They didn’t care.

Don’t succumb to SV hype - investors are (mostly) smarter than that.
How did we eventually raise?

Simple: we found true believers. @darian314 and @bubba put their name behind us after watching us for a year.

There is a “whisper network” amongst investors: they all share notes. If you want to raise a round, get into the network.
The “herd mentality”

Once you get your first yes, close everyone else quickly. If you have a good first investor, you should be able to close the round within 3-4 weeks.

Keep everyone updated with your progress, create momentum, and close as fast as possible.
Raising is only the beginning. The real work continues; take a moment to celebrate, then get back to building!

For practical stories about entrepreneurship, join my newsletter at

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More from @gaganbiyani

30 Sep
Most investors add no value, but when they do, it can be company-saving.

In 2010 as @udemy was just picking up steam, eBay-owned PayPal was cracking down on marketplace businesses for violating ToS. Without warning, they shut our entire payments system down.

**Read On**
We had a few months of runway and were starting to raise our Series A. It would take weeks to implement an alternative system, and that would've killed our traction story.

It was all-out panic mode.
We asked everyone for help - many were experiencing the same problem.

PayPal was notoriously bureaucratic at this time and was completely inaccessible to small startups like us.

The "best case" scenario, we heard, was 3 months of downtime.

That would've been a death blow.
Read 7 tweets
23 Sep
Yesterday I made a major life announcement: I’m starting a NewCo after 3 years of exploring

More of you cared than I expected; thanks for the support! 🙏🏾

What the hell did I do for 3 years?

Thought I’d share the back-story...

**Read On**
In 2017, my life blew apart as I shut down @Sprig. Shock + relief.

Even as we shut down, new opportunities were coming my way.

Funders for new ventures. Hotshot CEOs asking me to be an exec.

There’s always opportunity in SV.

What opportunities would I miss by stepping away?
After some good advice, I needed to resist the FOMO.

I know people who grinded for 20 years straight, constantly chasing more success and more money. That wasn’t for me.

I decided on the first rule of my transition: GET AWAY.

I packed my bags, left SF and went nomadic. Image
Read 14 tweets
9 Sep
In the 2001 recession, my parents lost everything, marriage included.

My dreams felt like they were slipping away; I was depressed, angry and had nowhere to turn.

This is a story about how I turned crisis into opportunity by fusing education and entrepreneurship.

**Read On**
I was in a tough spot. We didn’t grow up wealthy, but I certainly had enough. I went to good schools, traveled internationally, and had all the tech and books I needed.

The crisis threw a wrench in everything.

Like many people today, I started to question the status quo.
Slowly, I started to get pissed off. The world felt like it was out to get me. I questioned if the “adults” in the room knew as much as they purported.

My grades slipped and my rebellious nature came out.

It's so easy to devolve into anger when times are tough.
Read 19 tweets
30 Jul
Recently I've shared some heartfelt tweet-stories about entrepreneurship. Your support has been so encouraging 🙏🙏🙏

Now I'm doubling down with a personal mailing list: - please help spread the word!

**A thread on what will make this newsletter unique**
1. I'll talk about firsthand experiences.

There are great newsletters that opine about tech, startups, vc. Instead, I'm going to talk about in-the-trenches realities. Real shit that most newsletter writers haven't experienced or aren't willing to share.
2. Global.

Silicon Valley is an extremely insular place. I love it actually, but it isn't for everyone and isn't relatable. I've spent almost 4 years of my life abroad and been to 60 countries.

We're going to get outside the bubble.
Read 6 tweets
18 Jun
8 years ago, I got fired as President and co-founder of @udemy, a now-$2B unicorn

This is a tough story to share, and I’ll try my best to be honest

Fortunately this story ends on a positive note & I hope it’ll be useful to anyone who’s been laid off or fired.

**Read on**
I was just 21 when I met @erenbali + @caglaroktay.

I was a nobody, my family was broke, and I had never run a startup.

They, too, weren’t hot shots. Fresh off the boat from Turkey and still proving themselves.

They took a chance on me, and I on them.
Lucky for us, it worked out. @erenbali’s vision was spot on and slowly we raised some money and built out a team.

Nearly 2 million of you read this story already. It is posted here:
Read 24 tweets
27 May
Nobody talks about failure in Silicon Valley, yet 90% of startups fail.


3 yrs ago, @neerajberry and I shut down @Sprig, which raised $60M from @GreylockVC + @socialcapital & grew to $20m revenue.

Then, it all fell apart.

For an honest story about failure,

**Read on**
In 2013, I was @lyft, envious of how fast it was growing!

What about @lyft for food?

We looked @Postmates + thought:
- the food arrived sloppy / restaurants don't care about delivery
- it took forever (1hr)
- too expensive
We struggled through product iterations until we found "magic":

3 taps and $15 for a healthy meal delivered in 15 min

To make it possible, we had to run the restaurant ourselves; it would be expensive but worth it

We recruited @n8keller, Morgan Springer + @mattkent as founders
Read 20 tweets

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