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Service-to-SaaS Strategy: Bootstrapping to $5M ARR | Aditude

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Manage episode 488316192 series 61396
Content provided by Omer Khan. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Omer Khan or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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

This episode is brought to you by:

💖 GearheartBook a free strategy session + get 20% off select services

📫 MailtrapGet 20% off with code THESAASPODCAST

Resources:

🎧 Full Show Notes: saasclub.io/447

🎤 Subscribe to the Podcast: saasclub.io/subscribe

💌 Get weekly 5-minute SaaS insights: saasclub.io/email

💡 Join the SaaS Club founder community: saasclub.co/plus

  continue reading

629 episodes

Artwork
iconShare
 
Manage episode 488316192 series 61396
Content provided by Omer Khan. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Omer Khan or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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

This episode is brought to you by:

💖 GearheartBook a free strategy session + get 20% off select services

📫 MailtrapGet 20% off with code THESAASPODCAST

Resources:

🎧 Full Show Notes: saasclub.io/447

🎤 Subscribe to the Podcast: saasclub.io/subscribe

💌 Get weekly 5-minute SaaS insights: saasclub.io/email

💡 Join the SaaS Club founder community: saasclub.co/plus

  continue reading

629 episodes

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