Startup Funding Paths Quiz

Bootstrapping Your Way to Scale: Lessons from LeVar Burton and Mailchimp CEO Ben Chestnut

LeVar Burton, actor and educator, struggled to find funding for his kids' reading app and turned to Kickstarter, raising $6.4 million, with a significant contribution from Seth MacFarlane.
Burton's success with Kickstarter showed the power of turning to fans and supporters for funding when traditional investment fails to materialize.
Mailchimp CEO Ben Chestnut built a $600 million company without raising any outside funding, relying on a do-it-yourself ethos and a focus on simplicity and pragmatism.
Chestnut's early experiences with entrepreneurship included selling hand-drawn flipbook animations and working as a banner ad designer.
When Chestnut and his co-founder started their web design firm, they chose to find paying customers instead of seeking investment.
This early point is where entrepreneurs often overlook the option of seeking angel investment, which can bring valuable experience and insight to a growing business.
Bootstrapping takes time and can be a grind, as Chestnut and his co-founder learned in the early days of their business.
The dotcom bubble of the early 2000s made Chestnut wary of venture capital and influenced his decision to bootstrap the company.
Don MacKinnon, founder of Milq, also chose the endless angel route over formal Series A investment, adding small-dollar angel investors to his funding base.
Bootstrapping can be a viable option for entrepreneurs who want to grow at a moderate pace with contained risk, but it requires catching multiple waves of good fortune.
Successful bootstrapping requires a focus on simplicity and pragmatism, as well as a willingness to hustle and iterate rapidly.
While blitzscaling is a proven method of getting explosive growth, bootstrapping can be a viable alternative for entrepreneurs who don't want to take on outside investment.The Challenges and Benefits of Different Funding Paths for Startups
Having angel investors who understand the industry can provide valuable strategic advice and contacts, similar to a venture capitalist.
Managing the expectations of multiple angel investors can be a challenge, especially in a business with many unknowns.
Venture capital funding is best for rapid growth, but timing is key, and it may not be the right path if scaling is not part of the plan.
Mailchimp's founders initially struggled to scale their web development business and built their own in-house email software for clients.
Accepting credit cards for Mailchimp solved a major problem and allowed the founders to turn the internal tool into a scalable product.
Mailchimp's revenue was growing while the consulting business was flat, prompting the founders to make the leap and focus on Mailchimp in 2006.
The founders were approached by venture capitalists but were skeptical, as they did not align with their vision for Mailchimp as a SaaS company for small businesses.
Finding investors who understand the product and personality is crucial for motivation and success.
Crowdfunding can be a viable funding option for early-stage entrepreneurs, but it requires caution and realistic funding goals.
Building a cheap, minimum viable product and testing, learning, and iterating can be effective for both blitzscaling and crowdfunding.
Fortune 100 companies also use crowdfunding for various stages of their products.
Only 1% of founders will ever raise venture capital, making it important to explore other funding options.The Bootstrapped Path to Scale: Lessons from Mailchimp
Crowdfunding allows companies to test demand for their product or service before investing in it.
Mailchimp initially chose to bootstrap instead of seeking VC investment.
Bootstrapping requires being scrappy and lucky, and cash helps catch up fast.
Mailchimp hired a rock star engineer to develop new features and kept costs down by riding the wave of managed hosting.
Mailchimp's customers were leaving for competitors, so they asked for feedback and implemented the most-requested features.
Mailchimp lacked money for a big PR push, so they relied on blogging, tweeting, and building a community of passionate fans.
Mailchimp hit upon the freemium model, offering a free but cut-down version of their service to supercharge user uptake, which helped them scale rapidly.
With VC backing, inefficiencies would have been ironed out earlier, but bootstrapping allowed Mailchimp to stay sustainable.
Freemium and virality work together, and the instrumentation of the freemium model is a compounding loop that requires cohort analysis and A/B testing.
With the right kind of investors backing a company, they can get more speed, support, and on-target advice.
Bootstrapping requires tenacity and skill, but investment can bring more opportunities for expansion and domination of new markets.
Masters of Scale is a WaitWhat Original podcast that explores the strategies and tactics used by successful entrepreneurs to scale their businesses.