Thank you for your question Jayashree - so much to unpack here, I’ll give it a go!
Before YCBM we had actually built another tool, whenisgood.net, which is still up and running (just about) and before that we’ve actually built a further 8 other products!
So my co-founder Keith was good at turning out products, we just hadn’t worked out how to turn them into businesses.
When we spun YCBM off from WhenisGood - the growth was palpably different - we had customer and take up immediately. i think the growth that year something like 2,000% (this was 2011) and in 2012, we knew that we had a product + customers = business.
Growth for us as always been built deep into the nature of online scheduling - one booking introduces our tool to a new person and we do around 1 million bookings a month, so we’ve been incredibly lucky that out the door we’ve had the viral loop to depend on.
But challenges with massive growth if you are bootstrapping is being able to plan ahead (ie hire) when you might not necessarily have the cash. We struggled with banks to lend us money, and eventually took out private loans to tide us over. But we broke even about 3 years ago which was a great feeling as the business model was tied to so many cost factors as well as potential for growth.
So investment in new infrastructure (we jumped ship into AWS a few years ago which took a big chunk of time and distraction)
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investment in a new pricing model (our previous model simply wasn’t scalable)
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investment in a new client-side app to handle all account holder settings etc
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building our APIs + R&D
these all took massive amounts of time and energy to get right, which we did under cover of long term bootstrapped investment rather than short term considerations/
Frankly, if we had had investors in the room we would have spent half the budget on sales and marketing. But we would be dealing with the same issues (shaky infrastructure, slow UI, complex pricing) at just a bigger scale so I’m glad we did it the way we did.
on a side note - one of biggest headaches ever has been sorting our billing and subscription solution (which we have in-house) so I definitely recommend looking at all the tools available 