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- The Accelerator Conundrum
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- The Future: End of Capitalism
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bootstrapping with a paycheck
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 7)
Sramana Mitra: What kind of numbers did you do in 2016, 2017, and 2018? What was the ramp in terms of free users and paying users? What was happening? Ryan Chan: We’ve been growing very fast. We’ve hit a true nerve in this market and the completely underserved industry. Over 2,500 paying companies use UpKeep.
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 6)
Sramana Mitra: You have $10 million in the bank. You started hiring sales people and started putting a process together. Now, let me reask the question. What was the repeatable sales process?Was it that you started putting in a process to take all the leads? Are the free users categorized by companies, company size, and
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 5)
Sramana Mitra: Kevin was also doing YCombinator? Ryan Chan: I was part of the YCombinator class of winter ’17. Sramana Mitra: But you didn’t hire him through YCombinator. You hired him and brought him into your YCombinator membership. Ryan Chan: Right. We went through YCombinator. It was an amazing experience. I got introduced to this
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 4)
Sramana Mitra: What did you learn as you went through the customer base, started getting to know the customer base, understanding the customer base, and understanding who’s converting from free to premium? What did you learn in terms of who were the ones that were really important for the business from a segment point of
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 3)
Sramana Mitra: What did you do when that aha moment came? Ryan Chan: I hadn’t talked to this friend of mine in almost three years. He said, “Ryan, I will give you a little bit of money if you quit your job today and start working on Upkeep.” I did. I quit my job working
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 2)
Sramana Mitra: So you started building. Did you still have your day job? Was this on the side? Ryan Chan: This was a hobby on the side. I did this from 6PM to 10 PM, three times a week. I love learning things. I love building. For me, it was fun. I loved doing this.
Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 1)
If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Ryan took a hobby project that he bootstrapped with a paycheck and managed to get into YCombinator. From there, he raised a $10M Series A from a top-tier Silicon Valley firm, Emergence Capital. Excellent execution thus far. Sramana Mitra: Let’s start from the very beginning of
Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal (Part 6)
Sramana Mitra: How big a company do you think you can build? Obviously, you probably have a sense of the total market that you can access. What is the size of that market? Gene Caballero: The landscaping industry is about a $9 billion a year industry. Our TAM is almost limitless. In 2019, we want
