The Benefits of Bootstrapping

This past week I attended one of the knowledge share sessions hosted by Midwest House and was really inspired by the speaker, Matt Gira. He talked to us about founders that had bootstrapped their companies to 250k+ revenue in a little over 2 years. Venture capital often dominates the funding conversation, but for many startups, this model leads to unsustainable growth, loss of control, and ultimately, failure. At hili, we’re choosing a different path—one focused on long-term profitability, sustainable growth, and a product that genuinely serves our users.

Why We’re Not Seeking Institutional Funding

The downfall of high-profile VC-backed companies like Humane, alongside the growing frustration with tech ‘enshitification’—where companies shift value away from end users and business customers to itself—shows why startups need to rethink their funding strategies. We believe that sustainable businesses are built on real revenue, not investor expectations.

VC-backed startups often prioritize rapid scaling, user acquisition, and inflated valuations over building a solid, profitable business. According to a 2023 study by Startup Genome, 74% of failed startups cited premature scaling as a key reason for their downfall. At hili, we are committed to growing within our means, focusing on customer value, and ensuring that we build something lasting.

Building a Product People Love

Today, Google has a 90% search market-share by spending tens of billions of dollars in order to ensure that they are the default search engine behind every search box you encounter on every device, every service and every website. By having that kind of monopoly they are not incentivized to make their product better and Google’s search is, in fact, getting progressively worse.

Rather than chasing unrealistic growth metrics dictated by investors, hili is prioritizing building a product that people actually want to use. We believe that listening to our customers and aligning that with our company priorities will create a loyal user base that will continue to expand sustainably over time.

Lessons from Successful Bootstrapped Start-ups

Many successful companies have taken the bootstrapped path and thrived. Basecamp, Mailchimp, and Balsamiq have all built sustainable businesses without external funding. More recently, Karri Saarinen wrote an excellent post outlining Linear’s path to building a profitable company. Their success proves that bootstrapping isn’t just a viable option—it’s a powerful competitive advantage.

Why This Matters

By bootstrapping, hili can:

  • Remain independent: We answer to our users, not investors.

  • Prioritize quality: No rushed product decisions to satisfy external pressure.

  • Grow sustainably: Ensuring long-term stability for our platform and community.

We believe that the best way to build something meaningful is by staying in control, focusing on delivering real value, and ensuring our business is self-sustaining. While we are committed to bootstrapping, we recognize that funding can take many forms beyond traditional VC. Strategic partnerships, grants, revenue-based financing, and founder-friendly investment models are all viable ways to support sustainable growth while preserving our mission and values. In an era where tech companies are crumbling under the weight of VC expectations, hili is choosing a smarter, more sustainable path—one that puts our users first.

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Finding My People: What I Learned Navigating SXSW as a Female Founder

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hili made the Midwest Madness Top 64!