Timing your bootstrap with Calendly’s Tope Awotona and OpenView’s Blake Bartlett at TC Early Stage – TechCrunch


Once the trail much less traveled, bootstrapping immediately has change into a way more viable and widespread method to constructing a startup. By not taking enterprise capital {dollars} early, bootstrapping can drive founders to stay disciplined in serving their paying prospects properly. It’s additionally a fairly compelling method to decrease dilution for founders and early staff. No marvel then {that a} crop of unicorn enterprise startups has taken this street these previous years.

Few firms in that rising crop although have reached fairly the stature of Atlanta-based Calendly. The firm is not only on everybody’s calendars (actually), however has additionally change into a $three billion unicorn behemoth with $70 million in subscription income in 2020.

To get Calendly began, CEO and founder Tope Awotona raised $550,000 (which included his life financial savings) to get the corporate off the bottom, and remained bootstrapped for about seven years before inking a $350 million venture round with OpenView’s Blake Bartlett earlier this year along with Iconiq. OpenView occurred to be one of many few buyers within the firm’s single seed spherical as properly.

Bootstrapping is a steady dedication to not take enterprise capital for an prolonged time period. Why make that dedication? How does a founder construct the fortitude to withstand the lucre of VC when it may possibly make so many issues simpler? What are the benefits to bootstrapping, and when does the calculus change from avoiding VC to embracing it?

I’m excited to speak about these questions and extra with Awotona and Bartlett at our upcoming Early Stage — Operations & Fundraising event, the place we discover methods to reply the strategic and tactical questions that founders should make in the midst of main their startups.

Not solely will we be getting Awotona’s deep perspective as a founder, however we’re additionally going to dig into Bartlett’s long-time relationship with Calendly and how he assiduously constructed a partnership there over a few years to “win” what was one of many marquee offers of the 12 months. Bartlett has backed a wide range of main enterprise startups, reminiscent of Expensify (which has additionally demurred from the excessive stakes world of big-dollar VC), Highspot, Postscript and others, and I’m curious to see how he thinks about firms that go massive with enterprise versus those that wish to go massive with out it.

While many selections when constructing a startup may be delayed, the way you fund your startup (and due to this fact, the way you fund your staff and progress) is one which have to be made early and persistently. Join us and study extra in regards to the totally different paths to financing startups, and how one calendar firm timed its method to greatness.


The TC Early Stage curriculum is being unfold throughout two occasions, with fundraising and operations represented on April 1 & 2 and fundraising and advertising deep dives on July 8 & 9. Folks who purchase a ticket to only one occasion will get three months of Extra Crunch at no cost, and people who purchase a dual-event ticket will get six months of Extra Crunch membership at no cost.


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