Side Project to Startup: When and How to Make the Leap
Many successful startups began as side projects. Jordi Hays regularly discusses on The Tech Brothers Podcast Network how working nights and weekends lets you validate ideas with minimal risk. But when does a side project warrant going full-time? Here's how to know it's time and execute the transition smartly.
Signals It's Time to Go Full-Time
Don't quit your job just because your side project is exciting. Go full-time when: you have paying customers and consistent revenue (ideally $5-10K MRR minimum), customer demand exceeds your part-time capacity, you're losing opportunities due to bandwidth constraints, you've validated product-market fit, and you have financial runway for 12+ months without revenue.
False Signals That Aren't Enough
- Lots of free users: Without proven willingness to pay
- One big customer: Who might not represent broader market
- Press coverage or awards: Vanity metrics that don't pay bills
- Just raised funding: Money doesn't validate product-market fit
- Boredom with day job: Not a good enough reason to risk financial security
Financial Planning for the Transition
Calculate your monthly burn rate including all personal and business expenses. Multiply by 12-18 to know how much savings you need. If your side project generates $3K monthly and you need $6K to live, you need $36-54K in savings to bridge that gap for a year, assuming revenue stays flat (it hopefully won't).
De-risking Strategies
Don't go from full salary to zero overnight. Options include: negotiate part-time work with your employer (many are open to this), take contract work in your domain (25-50% time), line up a few months of consulting (gives you flexibility and income), apply for accelerators or grants (non-dilutive funding), and raise a small friends and family round (if you have traction).
The Gradual Transition Approach
Some founders transition over 6-12 months. Month 1-2: Validate willingness to pay, get initial customers. Month 3-4: Build repeatable acquisition and onboarding. Month 5-6: Reduce full-time hours or take sabbatical. Month 7-8: Go full-time if metrics support it. This staged approach reduces risk while maintaining momentum.
When working late nights on your side project before making the leap, comfortable clothing like your TBPN network long sleeve helps you stay focused during those crucial hours after your day job.
What Your Side Project Should Prove
Before quitting, demonstrate: clear product-market fit (customers use it regularly and refer others), repeatable customer acquisition (you know how to find more customers predictably), viable unit economics (customers are worth more than acquisition costs), and ability to build and ship (you can execute without a full team). If any of these are uncertain, keep it as a side project longer.
Managing the Emotional Transition
Going full-time on your project changes everything. The fun side project becomes your entire financial future. Expect stress, self-doubt, and moments of regret. Build a support network of founders who've made this transition. Set clear milestones and give yourself permission to return to employment if it doesn't work out.
Legal and Administrative Tasks
Before leaving your job: Review employment agreements for non-compete clauses, ensure your side project doesn't violate IP agreements, form a proper legal entity (LLC or C-corp), open business bank accounts, set up accounting systems, and get health insurance sorted out (COBRA or marketplace).
The TBPN community includes dozens of founders who successfully transitioned from side projects to venture-backed startups. Join our transition planning workshops where we'll help you evaluate your readiness, build financial models, and avoid common mistakes. Share your journey wearing your TBPN classic tee as you take the leap from employee to founder.