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Listen and learn from two techies with nothing to lose.

Whether you're an industry professional or a tech enthusiast, this podcast series offers a rare glimpse into the minds of two thought leaders shaping the future of multifamily housing.

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Bootstrapping Versus Capital Raising: The Crossroads of Vision and Growth

Join Kerry W. Kirby and Jimmy Lancaster, the masterminds behind the Multifamily Tech Gurus Podcast Series, as they explore the critical decision every entrepreneur faces: whether to bootstrap or raise capital to grow their business and how this choice can shape the future trajectory of a company, influencing everything from its growth rate and control dynamics to its long-term sustainability and impact on the industry.

Kerry and Jimmy unpack the concept of bootstrapping, where founders rely on personal savings, revenue, or other non-traditional funding sources to fuel their business. They also discuss the significant challenges, including slower growth and the constant pressure of managing cash flow, that it brings. On the flip side, they explore the path of raising capital, whether through venture capital, private equity, or other means, which can provide the financial resources necessary to scale quickly, hire top talent, and expand into new markets.

Kerry and Jimmy’s Words of Wisdom: "Ultimately, the choice between bootstrapping and raising capital is not just about financial strategy—it’s about the kind of company you want to build and the kind of founder you want to be. Both paths have their merits, and both can lead to success. The key is to choose the one that aligns with your vision, your values, and your long-term goals. In the end, it’s not just about reaching the destination—it’s about how you choose to get there.”

Resources: Bootstappers Have Freedom to Innovate

About The Hosts

Kerry W. Kirby

Kerry W. Kirby

Kerry W. Kirby is a renowned entrepreneur, technology innovator, and philanthropist. He is the founder and CEO of 365 Connect, a global leader in providing the most advanced automated marketing, leasing, and resident engagement platform for multifamily housing communities. Executing on a progressive vision of creating leading-edge products and services, Kerry has won more technology awards than any other company in his home state, as well as the industry he serves.

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Jimmy Lancaster

Jimmy Lancaster

Jimmy Lancaster is one of the most well-known engineers on the Silicon Bayou, specializing in custom software development. He specializes in building high-performance teams that deliver results and exceed expectations. He is the Chief Product Officer of 365 Connect, a global leader in providing the most advanced automated marketing, leasing, and resident engagement platform for multifamily housing communities.

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