548th 1Mby1M Entrepreneurship Podcast with Lloyed Lobo, Co-Founder of Boast.ai (Part 5)

Sramana Mitra: How did you manage the early phase where you had to stay afloat to get paid?

Lloyed Lobo: With the help of loans, houses bank loans, credit cards, and very lean teams.

Sramana Mitra: How many were you?

Lloyed Lobo: When we started, it was just me and my co-founder. Then there was a whole bunch of people. It was hard making payroll. A lot of credit to my co-founder because he funded it out of his personal cash to make payroll many times. We also got loans on my house and Alex’s house. They were very hard times. One of the things for us was our wives have been very supportive.

My co-founder’s wife is a GC at a public company. My wife is an ER physician at Stanford. They’ve been very supportive. One of the key learnings is, if you want to build an entrepreneurial venture and you want to bootstrap, make sure you have a supportive spouse.

Sramana Mitra: Somebody has to pay the bills in the family. That’s one of the things that we talk about all the time. What you’re pointing to is bootstrapping with a paycheck. In this case, bootstrapping with a spouse’s paycheck.

Lloyed Lobo: We didn’t use their paycheck to pay employees and business expenses, but they supported the lifestyle at home.

Sramana Mitra: Exactly, somebody has to pay the bills for the family. It’s all very well to say that you have to jump in with both feet, but how do you keep your life afloat?

Lloyed Lobo: Exactly. We had been a part of venture-backed failures. We really pushed the bootstrapped mode. If you build a product or service that people want, money will follow. A big part of our growth strategy has been community-led growth. We sell to founders and CEO’s of technology companies. When we started the company, we started doing pizza nights. It would not be on R&D credits; it would be on some topic.

The CEO of a tech company needs more than just R&D credits. Those pizza nights kept growing. It has evolved into a big community today. We have about 115,000 subscribers. We never call that community. Today, we do two webinars a week. We do monthly dinners in different cities, conferences, and popup events. Every major tech CEO from Twilio to Zoho has come to our event. We donate the money from it, but that community growth has been a big part of our revenue growth.

Sramana Mitra: How long did you have to operate in this lean mode and struggling to meet payroll?

Lloyed Lobo: Till about 2018. It was tough. We raised the $23 million Series A in November 2020. When we raised the money, we had 30 people. Now we’re over a hundred people. Our CTO joined us from Avalara. We have a very active Board Member who sold her company for a billion dollars. Previously, she was the SVP at Intuit. We brought in a very solid team. It’s a different story now.

This segment is part 5 in the series : 548th 1Mby1M Entrepreneurship Podcast with Lloyed Lobo, Co-Founder of Boast.ai
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