Blakely Graham co-founded TaskRay, a project management and customer onboarding platform built inside the Salesforce ecosystem. After years working with Salesforce implementations and operations teams, she and co-founder Eric Wu saw a major gap between closing deals and successfully onboarding customers. They bootstrapped the company from a simple Kanban-style workflow app into a growing SaaS business serving increasingly complex enterprise implementations.

TaskRay started with self-serve AppExchange purchases and evolved into enterprise software with six-figure contracts, serving companies with sophisticated onboarding and delivery needs. The company stayed profitable from the beginning, grew to roughly 40 employees, and eventually reached nearly $10M ARR. A major turning point came when the team repositioned around "customer onboarding" instead of generic project management, dramatically improving focus, retention, and enterprise growth.

Blakely also shares the difficult founder realities rarely discussed openly: co-founder conflict, burnout, loneliness, identity shifts, and the emotional weight of leading a growing company for more than a decade. After stepping away following the 2021 sale of TaskRay to a search fund-backed buyer, she focused on recovery, advisory work, and co-hosting the Not All Business podcast to help founders and leaders feel less isolated during difficult growth stages.

Key Takeaways

Focus to Grow Faster — TaskRay discovered its strongest positioning by focusing narrowly on post-sale onboarding instead of generic project management.
Bootstrap Discipline — The company stayed profitable from day one by growing carefully, shipping quickly, and avoiding unnecessary complexity early.
Founder Burnout — Burnout showed up as physical exhaustion, emotional numbness, and losing the energy to inspire teams or create new ideas.
Co-Founder Conflict — Long-term founder relationships can fracture under pressure, but respect and self-awareness can rebuild trust over time.
Invest In Yourself — Peer groups, coaching, therapy, and personal health practices are essential leadership tools, not optional luxuries.

Quote from Blakely Graham, Co-founder of TaskRay

"This is probably the most important thing I learned as a CEO, and, I swear founders can't hear it. They just can't hear it.

"You have to invest in yourself. The word "self care" drives me crazy because that's what people told me for 10 years. Self care. What are you doing for self care? I'm like, I don't know. Leave me alone. I don't have time, any down time.

"Well, of course sitting on the other side of burning out and selling my company, founders just have to invest in themselves in the journey. It can be a peer group, it can be a coach. can be therapy. Heck for me, it's nature walks and going to the gym. Just do it because people don't want you to burn out. They want your leadership, so you have to invest in yourself and don't feel guilty about it. There, I said it."

Links

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