Episode 705 | From Bootstrapped to Mostly Bootstrapped to Venture Backed

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Mar 19, 2024

Braden Dennis, co-founder and CEO of FinChat, shares insights from his journey of evolving a bootstrapped startup into a venture-backed company. He discusses the importance of starting with an existing audience and how they successfully launched a second product. Braden emphasizes the strategic decisions that shaped FinChat's growth, including navigating funding options and the benefits of having multiple co-founders. His experience highlights invaluable lessons in product development and the challenges of maintaining flexibility in a scaling business.

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ANECDOTE

From Podcast to SaaS

FinChat, initially Stratosphere, started as a tool for Braden Dennis's investing podcast.
It leveraged an existing audience for initial product development and feedback.

ADVICE

Audience Advantage, But...

While an existing audience can help with initial SaaS launch, don't solely rely on it.
Focus on broader marketing strategies like SEO and product development for long-term growth.

INSIGHT

Upmarket Pivot

FinChat's initial target audience, retail investors, limited its growth potential.
Moving upmarket to serve professional investors opened doors to higher pricing and scalability.

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In episode 705, Rob Walling interviews Braden Dennis, co-founder and CEO of FinChat. They discuss Braden’s journey going from fully bootstrapped, all the way to taking venture capital as FinChat scaled. Braden shares his experience in initially launching to an audience, how they successfully launched a second product, and how FinChat operates well with multiple co-founders.

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Topics we cover:

2:55 – What does FinChat look like today?
4:00 – Starting with an audience and building a SaaS
6:40 – Formulating the product and moving upmarket
8:35 – Launching a second product
12:25 – The common pitfall of launching a second product
16:25 – How FinChat found explosive growth
19:27 – Deciding to take venture funding
26:13 – Making hard decisions with incomplete information
30:31 – Working with multiple co-founders

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If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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