Side Hustle School Ep. 3565 - First $1,000: “I got paid to walk dogs while on work calls…”
5 snips
Oct 5, 2026 Raina Silvante is a Chicago-area entrepreneur with a master’s degree and a professional day job who launched Day Job Dog Walkers during the pandemic. She shares how flyers, neighborhood posts, and a memorable name brought in clients while she worked remotely. The business grew past $15,000, eventually involved hiring help, and boosted her confidence as an entrepreneur.
AI Snips
Chapters
Transcript
Episode notes
Start With An Accessible Side Hustle
- Side hustles can begin with accessible, low-pressure experiments rather than ambitious business plans.
- Chris Guillebeau introduces Raina Silvante’s pandemic dog-walking story as an example of earning extra income without quitting a job.
Why Raina Started Walking Dogs
- Raina Silvante chose dog walking because it felt accessible and non-intimidating after earlier projects stalled.
- Her neighborhood’s many dog owners and abundant remote-work downtime created an unusually convenient starting market.
Find Customers Through Local Channels
- Test a simple service in the places where potential customers already gather.
- Raina used coffee-shop and street-pole flyers plus the neighborhood Nextdoor app, producing her first few customers without overthinking.