"Our data is powering the infrastructure of this massive new market."

"Building Data-as-a-Service is a very, very hard business."

"difficult problems have big rewards"

"You're making decisions on complete gut."

Braden Dennis is the true definition of an entrepreneur. He started a podcast in his college dorm room and now runs an industry leading Fintech. Fiscal.ai has pivoted three times since inception and is now focused on building the latest generation financial data company using delivery speed and rapid product iteration as its competitive advantage.

Companies mentioned: Google Finance ($GOOGL), Claude, OpenAI, Bloomberg, Fiscal AI, Perplexity.

Thank you to Fiscal.AI, our sponsor of the Wall Street Entrepreneur series!

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Highlights

[00:00:18] Introduction to Braden Dennis and Fiscal AI

[00:01:44] Braden Dennis's investing background and early podcasting journey

[00:02:58] Influential investing books and lessons that shaped his entrepreneurial approach

[00:05:27] Overview of Fiscal AI's financial data business and competitive advantages

[00:07:29] Origins of Stratosphere and the launch of FinChat

[00:08:39] FinChat's viral growth following the release of large language models

[00:11:09] Raising seed capital and demonstrating early startup traction

[00:11:27] Product-market fit and the importance of rapid iteration

[00:13:22] Advice for founders on fundraising and seed-stage milestones

[00:15:26] Why the company shifted from a retail investing platform toward data infrastructure

[00:16:07] Building proprietary financial datasets and owning the underlying content

[00:19:11] Transitioning from software subscriptions to B2B data feeds

[00:20:00] Startup decision-making, uncertainty, and operating on imperfect information

[00:21:59] Startup moats, competition, and scaling from zero to one

[00:24:09] Customer retention, activation, and key business metrics

[00:25:52] AI infrastructure, token usage, and building data products at scale

[00:28:32] Product roadmap, data coverage expansion, and competitive positioning

[00:30:18] MCP integrations and delivering financial data directly into AI workflows

[00:31:36] Global data coverage, ownership data, transcripts, and company KPIs

[00:34:22] Total addressable market for financial data and long-term revenue goals

[00:36:40] Scaling from $10 million to $50 million in annual recurring revenue

[00:38:41] Creating a news product focused on signal rather than noise

[00:42:36] Managing emotions and maintaining perspective as a founder

[00:43:23] Leadership lessons and the risks of impulsive decision-making

[00:44:18] Demonstration of Fiscal AI's terminal, API, and investor tools

[00:46:37] AI-powered research workflows using Claude, Codex, and MCP integrations

[00:49:27] Data ownership, model training, and the value of accurate financial information

[00:53:00] Handling adjusted financial metrics and analyst workflows

[00:53:58] Building custom investor dashboards and the future of AI-assisted research

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Pitch The PM Links:

📩 Subscribe to our Substack for research updates and new high-conviction episodes from top PMs, and our Job Board: ⁠https://pitchthepm.substack.com/⁠

Doug Garber on LinkedIn: https://www.linkedin.com/in/doug-garber-42aa508

Fiscal.AI Links:

Braden Dennis on LinkedIn: https://www.linkedin.com/in/braden-dennis-881a88b0/

Fiscal AI - https://fiscal.ai/

EP. 42: Building Data-as-a-Service using AI tokens–Making Decisions on Complete Gut!

Pitch The PM

EP. 42: Building Data-as-a-Service using AI tokens–Making Decisions on Complete Gut!