How Jason Buckingham found a SaaS idea through 70 cold calls

Executive overview

Most founders stumble on ideas through their own problems. Jason Buckingham had no idea and no existing customer relationships — so he cold-called his way to one.

After 35 fruitless calls in home care, a single conversation revealed senior placement as an underserved niche. Another 35 calls confirmed the problem. He pre-sold the product before writing a line of code.

Persistence without a shortcut — making 70 cold calls while holding a day job — is a valid path to a fundable SaaS idea.

The cold outreach process that worked

• Targeted home care company owners by searching online directories, not warm introductions
• Emails were short, personalized, and asked for 15 minutes to learn about their day — not to pitch
• High response rate because he was only asking to talk about them
• On calls, he never talked about himself; he listened and took handwritten notes
• 35 calls with home care showed one vendor already dominated the market — he didn't quit, he pivoted

Discovering senior placement

• On call 35, a home care owner mentioned they also did senior placement — acting as realtors for elderly people moving into assisted living
• Jason had never heard of the industry; the contact said it was fast-growing and underserved by software
• He ran another 30–40 calls with placement agencies across the country
• Every call confirmed the same core problem: no good way to track clients and match them to communities
• Early calls done at 6–7am to catch East Coast contacts before his Microsoft day job

Validating with pre-sales

• After partnering with developer friend JD (also at Microsoft), they built mock-ups before writing any code
• Met one prospect in person at a coffee shop, demoed mock-ups on a tablet — she brought two employees and wrote a check on the spot
• Pre-sold to five customers at a 20% lifetime discount in exchange for upfront payment
• One of the five later pivoted her business and never onboarded; the other four are still customers five years later
• Pre-sales were about commitment, not cash — skin in the game before hundreds of hours of building

Building while employed

• Both founders worked 40 hours a week at Microsoft and 30 hours a week on Senior Place
• Jason's routine: family dinner, kids to bed, an hour with his wife, then coding until 2am
• No TV, no movies, no video games — deliberate sacrifice for a defined period
• Kept the day job as a funding mechanism; used their own salaries rather than hiring contractors they weren't satisfied with
• Being picky developers, they delayed hiring and stayed at day jobs longer than ideal

Keeping a spouse on board

• Discuss the plan before the grind starts — easier to get agreement before the sacrifice is real
• Regular check-ins matter more than the initial conversation
• Scheduled a long weekend away with his wife mid-journey to reset the relationship
• Daily habit: an hour of conversation with his wife after kids were in bed kept the connection intact
• The goal was to be present for his family — not to sacrifice family for the startup

Slow growth and the COVID pivot

• Growth was slow because the two founders were splitting time across coding, marketing, and customer support simultaneously
• Customers in this niche had unique, highly variable needs — forcing customization that slowed progress
• Applied to Tiny Seed (batch spring 2020), were accepted, signed paperwork, money was wired
• Jason gave two months' notice at Microsoft; COVID hit; placement agencies stopped getting referrals as families kept elderly relatives home
• Lost five customers in one week — more than in the previous three years combined
• Returned the Tiny Seed money and withdrew notice; his manager hadn't found a replacement yet

Recovery and second Tiny Seed batch

• Roughly doubled revenue in 2020 after the initial COVID shock stabilized
• Reapplied to Tiny Seed for the spring 2021 batch and were accepted
• Left Microsoft after 15 years in April/May 2021 — no farewell lunch due to remote work, just a Teams call
• Team is now four: two co-founders, one contractor developer, one support and onboarding hire
• Near break-even at time of recording, with partnerships expected to significantly increase MRR

What makes Senior Place's market unusual

• Customers are predominantly women in their 50s–60s, many not technically confident
• Website uses a handwritten font and simple design — intentional, not an oversight; matches the demographic
• "Me and computers aren't even acquainted, but your software is so easy to use" — direct customer feedback
• Near-zero churn: no customer lost to a competitor in two to three years
• Low-tech customers who find a tool that works almost never leave — customer pain markets have brutal acquisition but exceptional retention