Jared Siegal, founder and CEO of Aditude, shares his journey from consulting to a successful SaaS business. He emphasizes the importance of offering value to build trust and discusses the challenges of scaling and delegating responsibilities. Siegal reveals how events can foster client relationships, plus insights into navigating capital and maintaining product stability before seeking investment. He also touches on the impact of AI and his personal battles with multiple sclerosis, showcasing resilience and the drive to innovate.
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question_answer ANECDOTE
Impulsive Start to Consulting
Jared Siegal quit his job impulsively after his boss denied a raise and started consulting friends in the publishing space.
He ran this hourly consulting business solo for about a year before hiring one employee.
question_answer ANECDOTE
Turning Down Acquisition Offers
Jared received multiple unsolicited acquisition offers for his consulting business but declined them to build a SaaS product.
He did not fully know what SaaS meant but convinced his friend to join as CTO and start building the product.
volunteer_activism ADVICE
Give Product Free Then Monetize
Give your product away for free initially to build trust and prove its value to customers.
Use the free usage period to convert all clients to a paid SaaS model once the product demonstrates clear revenue benefits.
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Jared Siegal got his first customers by giving his product away for free—then converted every single one of them to paying subscribers in four months. In this episode, early-stage B2B SaaS founders will learn how to acquire first customers without spending on sales or marketing.
Jared breaks down exactly how he turned 30 consulting clients into his first customers using a "Trojan Horse" strategy. You will learn how to borrow resources from clients to build your MVP, why giving your SaaS away for free creates unbreakable stickiness, and the negotiation leverage that comes from being profitable before raising capital.
In this episode, Jared also shares the "Disney World strategy" that creates client loyalty beyond contracts—some of his first customers have literally written him into their wills.
🎯 Get First Customers by Giving Your Product Away: Jared gave his SaaS away for free for six months, making clients completely dependent on his tech—100% converted when he started charging.
💰 Use Consulting Revenue to Fund First Customers: Jared used $2M/year in consulting revenue as his own VC fund—no investors, no dilution while acquiring his first customers.
🛠️ Borrow Resources from First Customers: Jared got a client's engineer for free for six weeks by aligning incentives: "If this works, you save money."
📈 Be Profitable Before Raising Capital: Jared waited until $5M ARR to raise his Series A. His advice: "If you're profitable, you control the negotiation."
🤝 Build Relationships That Transcend Business: The "Disney World strategy"—annual trips with clients—creates loyalty that goes beyond contracts.
🧠 Let Go to Scale: A forced two-week vacation taught Jared the company could run without him—essential for scaling beyond founder-led operations.
Chapters
Introduction & The "Luke Bryan" Quote
From Employee to Scrappy Consultant
Three Acquisition Offers in One Month
Borrowing a Client's Engineer to Build the MVP
The Deep Client Relationships: "I'm in Their Wills"
Converting First Customers: From Free to Paid SaaS
Hitting $1M ARR in Four Months
The Pain of Bootstrapping & Personal Financial Risk
The SaaS Podcast: Build, Launch & Scale Your SaaS