Best of Bootstrapping: Bootstrapped to YC and a $10M Series A

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

UpKeep Founder CEO Ryan Chan took a hobby project that he bootstrapped with a paycheck and managed to get into Y Combinator. From there, he raised a $10 million Series A from a top-tier Silicon Valley firm, Emergence Capital. Excellent execution as of this podcast interview from 2019.

Sramana Mitra: Let’s start from the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Ryan Chan: I was born in Kentucky. My family moved there for my father’s job. But then, we quickly relocated to California. I grew up and was raised in a small suburb in Los Angeles called Oak Park. Not many people know where that is, but it’s about 20 miles west of downtown Los Angeles.

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Best of Bootstrapping: Bootstrapped an E-commerce Business to $12M

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

What a wonderful story of an e-commerce company bootstrapping to $12 million from a small town called Horsens in Denmark. When we spoke in 2019, all of the 60 employees working under Trendhim CEO Sebastian Petersen were working out of Horsens.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Sebastian Petersen: I’m from Denmark. I would say I had a pretty ordinary background. Both my parents were working in the public sector. I’ve always had an entrepreneurial spirit together with one of my best buddies growing up. We were always together.

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January 11 – 629th 1Mby1M Mentoring Roundtable for Entrepreneurs

Entrepreneurs are invited to the 628th FREE online 1Mby1M Mentoring Roundtable on Thursday, January 4, 2024, at 8 a.m. PST/11 a.m. EST/5 p.m. CET/9:30 p.m. India IST.

If you are a serious entrepreneur, register to “pitch” and sell your business idea. You’ll receive straightforward feedback, advice on next steps, and answers to any of your questions. Others can register to “attend” to watch, learn, and interact through the online chat.

You can learn more here and REGISTER TO PITCH OR ATTEND HERE. Register and you will receive the recording by email, even if you are unable to attend. Please share with any entrepreneurs in your circle who may be interested. All are welcome!

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628th 1Mby1M Roundtable Recording

In case you missed it, you can listen to the recording of this roundtable here:

Best of Bootstrapping: The Journey Through Failed Experiments to Traction and Exit

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

Entrepreneurs love to discuss success. Few are willing to discuss what they tried and failed at. When we spoke in 2019, Robly Co-founder Adam Robinson did a terrific job of sharing his journey through various failed experiments to a model that was gaining traction. Robly was bootstrapped to an 8-figure exit to private equity in 2021.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Adam Robinson: I was born and raised in Houston, Texas. I went to Rice University. I graduated in 2003. One of my friends had an internship at Goldman-Sachs the year before. I didn’t know anything about it, and somehow convinced people to give me a job as a derivatives trader at Lehman Brothers. For 10 years, I traded these real estate-related, credit default swaps. It was the most interesting job for someone in their 20’s. Everybody who was doing what I was doing was making a ton of money.

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Catching Up On Readings: Biggest VC Funding Rounds in 2023

This report from Crunchbase looks at the top 10 VC funding rounds in 2023, many of which were for AI startups like $10 billion for OpenAI. For this week’s posts, click on the paragraph links.

Roundtable Recap: January 4 – Many Substantial Conversations on Startup Strategy

During this week’s roundtable, we had many substantial conversations on startup strategy based on specific startup scenarios. Much to learn from them.

Hample.com

We had Krishna Prasad from Ranga Reddy, India, pitching Hample.com, an e-commerce idea.

In general, all those of you who are getting yourselves ready to launch a venture, please study our material and get prepared with real knowledge. Do not shoot from the hip and make perfectly avoidable mistakes.

You can listen to the recording of this roundtable here:

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Best of Bootstrapping: Bootstrapped to Over $10M and a Big Exit

If you haven’t already, please study our free Bootstrapping Course and Investor Introductions page. 

CEO Carl Ryden and his co-founders had bootstrapped PrecisionLender to over $10 million from North Carolina when we spoke in 2017. This is a superb story, including how the company has formulated an AI agent, Andi. Q2 acquired PrecisionLender for $510 million in 2019.

Sramana Mitra: Let’s start at the very beginning of your personal journey. Where are you from? Where were you born, raised, and in what kind of background?

Carl Ryden: I was born in North Carolina. I grew up in eastern North Carolina in a little town called Goldsboro. Folks don’t know where that is. It’s about halfway between Raleigh and the coast. For folks who do know, I would later confess that I’m not really from Goldsboro. I’m from an area of a county that’s closest to Goldsboro, deep in the rural part of North Carolina.

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