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Fireside chat with Bridget Harris and Alex Theuma - How to take care of business: 5 lessons in bootstrapping to $5m ARR

5 lessons in bootstrapping to $5m ARR

Bridget Harris · YouCanBookMe

Published March 15, 2023
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Bridget Harris and Alex Theuma discuss bootstrapping from early capital constraints through team building, culture, and ownership decisions. The conversation stresses choosing a business model deliberately and understanding investor incentives before taking external capital.

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Stretching early capital

“experience of bootstrapping and I want to hear what you think about your timing for for because you were much more in the you need upfront Capital so I want to know how you did it um it just so happens that with our products we were doing online scheduling it's a drip drip it's a self-service it's a freemium so because of that and also we started about 15 years ago the timing for us to be able to stretch that out over a long time when you're really earning very little now for context to get that 5 million we have over 20 000 customers so we have a lot of small people Small Engines small amounts of”

Early team composition

“you need some kind of creative designer product owner or somebody who's going to sort of shape that product over time basically me and Keith had the had the first two so he was the engineer and I was the operations person and you see that today 10 years later in the in the company it's a very engineering and operations-led Company that's taken a while for us to move across into more product and design LED sort of set of priorities so you can get a lot of people but I don't I've never met somebody yet who's one person who's”

Building culture through opportunity

“that you can incentivize people to be a part of also don't underestimate the power of the offer to say you have an opportunity to really change something here you can come in here is here's here's the way we've laid it out because we've been bootstrapped we're not under any pressure to kind of deliver to an external person's criteria we can build something that we really want so one of our internal cultures and culture statements is um commitment to Excellence so that's that sometimes does mean we're going to rewrite something or we're going to drop it because it's not”

Understanding venture incentives

“card maybe maybe I would just say that's fine that's completely legitimate but you've got to be educated around the table if you're going to take money from a BC and I read about 10 years ago Venture deals whatever it came out read that book because um it will tell you exactly how deals are structured what the incentive of the VC is and what business that they're in and it's a really great business um it's a legitimate business but it's not necessarily got anything to do with what you've decided to sell as a product so um you just have to educate yourself”

Choosing your business model

“wrong and and you know you've got to take care of it at the same time you have to be philosophical like apart from anything else the perspective we were in business before calendly we've been in scheduling for a very long time and we our goals are different because we're bootstraps so I don't need to be a 200 million pound company in order for actually everybody who works for us and our customers to be super happy so you know I'm glad to see obviously Dingus and Sassy are in the room as well your money that's in our bank account that was in svb that we're protecting here”

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About the speaker
Bridget Harris

Bridget Harris

CEO & CoFounder · YouCanBookMe

Bridget Harris is the CEO and co-founder of YouCanBook.me - an online scheduling tool that helps businesses manage their customers and calendars. Bridget is the co-founder of YCBM, launched in 2012. Before then she had a career in parliament, government and politics as an advisor.

Company revenue
$5M
Team size
24

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