Jared Siegal quit his job on a whim to start a consulting business, grew it to $2M in revenue, and then successfully pivoted it into a high-growth SaaS platform. He bootstrapped Aditude to over $5M in revenue before raising a $15M Series A.

In this episode, Jared reveals the "Service-to-SaaS" playbook he used to transition from hourly billing to recurring revenue. He shares how he convinced a client to lend him an engineer for free to build the MVP, why he forced all customers to pay 100% upfront (creating negative working capital), and how he closes his biggest enterprise deals by taking prospects to Disney World instead of boring steak dinners.

🔑 Key Lessons

• 🚀 Service-to-SaaS Pivot: How to transition a $2M consulting firm into a scalable software business without losing revenue.


• 🛠️ The "Client-Funded" MVP: How Jared got a client to give him an engineer for 6 weeks for free to build the first version of the product.


• 💰 Cash Flow Strategy: Why he enforced a strict "Pay in Advance" policy to bootstrap to $5M without external capital.


• 🎢 Event-Led Growth: The unique strategy of hosting multi-day Disney World trips for prospects that converts better than traditional sales.


• 🧠 Founder Urgency: How a personal health diagnosis (MS) drives Jared's relentless focus on revenue over vanity metrics.

📖 Chapters

• Introduction and Favorite Quote


• Overview of Aditude's Product and Market


• Company Growth and Funding Journey


• Founder's Background and Early Career


• Transition to Consulting and Early Challenges


• Building the SaaS Product


• Client Relationships and Early Success


• Bootstrapping Challenges and Decision to Raise Capital


• Effective Fundraising Strategies


• Bold Outreach and Networking


• Targeting the Right Investors


• Referral-Based Growth


• Advance Payment Policy


• Event-Based Client Engagement


• Transitioning Leadership Roles


• Lightning Round: Business Insights

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Resources:

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