The Rise of Bootstrapping in Startup Culture

Historically considered an unconventional route, bootstrapping has evolved into a increasingly practical and widespread method for launching a startup. Choosing to forego early venture capital funding can instill a strong sense of discipline in founders, compelling them to prioritize the needs of their customer base. Furthermore, it presents a valuable opportunity to minimize equity dilution for both founders and initial team members.

Despite the growing trend, few companies have achieved the same level of prominence as Calendly, headquartered in Atlanta. The company’s scheduling software is ubiquitous, and it has attained a valuation of $3 billion, generating $70 million in subscription revenue during 2020.

Calendly’s journey began with a $550,000 investment from CEO and founder Tope Awotona, including his personal savings. The company remained bootstrapped for approximately seven years before securing a $350 million venture round led by Blake Bartlett of OpenView and Iconiq. Notably, OpenView was also an early investor in Calendly’s seed round.

Understanding the Bootstrapping Commitment

Bootstrapping signifies a sustained decision to abstain from venture capital for a considerable duration. What motivates this commitment? How do founders cultivate the resilience to resist the allure of VC funding, which could potentially streamline numerous processes? What benefits does bootstrapping offer, and at what point does the strategic consideration shift from avoiding VC to actively seeking it?

I am pleased to announce that these questions, and others, will be addressed in a discussion with Awotona and Bartlett at our upcoming Early Stage — Operations & Fundraising event. This event will focus on the critical strategic and tactical decisions that founders face while leading their startups.

Attendees will gain valuable insights from Awotona’s firsthand experience as a founder. Additionally, we will explore Bartlett’s long-standing relationship with Calendly and his deliberate efforts to establish a partnership over several years, ultimately securing a significant deal. Bartlett has also invested in other successful enterprise startups, including Expensify, Highspot, and Postscript.

The Importance of Early Funding Decisions

While certain startup decisions can be deferred, the method of funding – and consequently, the funding of employees and growth – is a crucial choice that must be made early and maintained consistently. We invite you to join us to learn about the diverse paths to startup financing and how one scheduling company strategically timed its approach to achieve success.

The TC Early Stage curriculum is structured across two events. The first, on April 1 and 2, will cover operations and fundraising. The second, on July 8 and 9, will provide in-depth explorations of fundraising and marketing. Purchasing a ticket to a single event grants three months of Extra Crunch access, while a dual-event ticket includes six months of Extra Crunch membership.

• Bootstrapping: Self-funding a startup without external investment.
• Venture Capital: Funding provided by investors in exchange for equity.
• Equity Dilution: The reduction in ownership percentage due to the issuance of new shares.