JIM JACOBSEntrepreneur, Operator & Creator of The Power of Ask
“Most people don’t miss out on the business or life they want because they lack talent. They miss out because they reject themselves before anyone else gets the chance. I built The Power of Ask so you have the exact words to make one professional ask and one personal ask before midnight tomorrow—and an Accountability Coach that follows up with you until you hit send.”
JIM’S OPERATING RULE
“Keep the dream big. Make the first ask small.”
The Story Behind The System
WHY AN ENTREPRENEUR BUILT AN ACCOUNTABILITY ENGINE FOR ASKING
Every major turning point in Jim’s career and personal life came down to asking a better question—First to people, and now to AI.
THE FIRST ASK · $5/HOUR COUNTER TO NETWORK TV
One Nervous Question Changed Everything
Working behind the counter at West Coast Video for $5 an hour and waiting tables at TGI Fridays, Jim asked Philadelphia sportscaster Gary Papa one question instead of talking himself out of it. That single ask opened the door to a career in live sports television alongside icons like Kobe Bryant, Michael Jordan, and Wayne Gretzky.
PERSISTENCE BEATS PRESTIGE · 20 ASKS, 19 NO'S, 1 YES
Why Rejection Is Just Data
When Jim set out to connect with Arnel Pineda, lead singer of Journey, it took 20 asks and 19 silences or no's on Instagram before landing the one yes that led to an unforgettable backstage friendship. You do not need 20 yeses—you only need one.
ENTREPRENEUR & OPERATOR · FOCUS INSITE & HUMAN LAYER AI
Building an Inc. 5000 Company & Leveraging a 24/7 AI Workforce
As Co-Founder & CEO of Focus Insite (an Inc. 5000 market research recruiting firm) and founder of Human Layer AI, Jim built real-world AI + human operating workflows that let his team say yes to a $65,000 rush project right before Labor Day with a 7-day deadline—proving what happens when you know how to leverage an unlimited workforce that works 24/7 for you.
WHY HE BUILT THIS PLATFORM FOR YOU
Don't Leave With Inspiration. Leave With an Ask.
After speaking to entrepreneurs and executives across EO, YPO, Wharton, Harvard, and MIT's Entrepreneurial Masters Program, Jim realized most people leave talks inspired—and then do nothing. He built ThePowerOfAsk.com and the AI Accountability Coach so every visitor walks away with one professional ask and one personal ask sent before midnight tomorrow.
EO Peer Note from Jim: Everything on this site is 100% free and un-gated for you to use with your leadership team. In EO fashion, there is zero pitch here—just experience share. If you ever want to look under the hood of how I run my 24/7 AI agent crew or talk through an impossible ask founder-to-founder, my door is always open: Grab 15 minutes or send me a note or email me directly at jim@flyingwiththehawk.com or jim@focusinsite.com.
WHAT HAPPENS WHEN YOUR ENTIRE TEAM LEARNS THE POWER OF ASK + THE POWER OF AI?
Most organizations sit on millions of dollars in unmade asks—and lose 80% of their week to manual prep and follow-up that an AI agent crew can run 24/7. When Jim Jacobs speaks to your company, EO/YPO chapter, or sales & leadership team, nobody leaves with just notebook inspiration. Every person in the room leaves with three concrete assets:
OUTCOME 01 · IMMEDIATE ACTION
1 Business Ask & 1 Personal Ask Sent Before Midnight
Built live in the room on their phone in 3 minutes (100% un-gated)—a clear, <75-word low-friction door opener plus a “19 No's to 1 Yes” follow-up script.
OUTCOME 02 · FOLLOW-THROUGH ENGINE
A 24-Hour Virtual Accountability Partner
Every participant gets an optional Virtual Accountability Partner (via Email, WhatsApp, or self-guided check-in link) that follows up 24 hours later so asks actually get sent.
OUTCOME 03 · 24/7 AI CAPACITY
Making the “Impossible” Possible With AI Agents
Your team learns how to turn a 1-person ask into a 24/7 AI workflow—researching targets, pre-building custom “give-first” deliverables in 10 minutes, and scaling capacity without adding headcount.
WHERE ONE ASK CAN TAKE YOU
From asking legendary sportscaster Gary Papa for a break at a $5/hour counter job—to interviewing Michael Jordan, Wayne Gretzky, and Kobe Bryant, appearing on CNN and in Forbes, walking onto Hollywood sets (Creed, Paranoia, Billions), scaling an Inc. 5000 company, and celebrating Flyers Cup championships with family:
WANT JIM TO TALK TO YOUR GROUP OR TEAM ABOUT THE POWER OF ASK OR THE POWER OF AI?
Whether you run a company leadership team, an EO / YPO chapter, a sales organization, or an industry association, Jim customizes every session so your people leave with:
- Live Interactive Ask Challenge: Every person builds and sends a real Business Ask & Personal Ask using The Ask Coach™ on their phone.
- Virtual Accountability Partner: 24-hour and 30-day follow-up so your team turns ideas into measurable revenue and partnerships.
- Practical 24/7 AI Agent Playbooks: Live demonstration of how Jim runs a 24/7 AI workforce to make “impossible” asks possible in 10 minutes.
Direct Founder-to-Founder Contact:
Email Jim directly at jim@flyingwiththehawk.com or jim@focusinsite.com, or use the quick form here (connected directly to Jim's GoHighLevel & inbox).
Operator Background & Credentials
Built From Real-World Operations—Not Theory
- Co-Founder & CEO, Focus Insite (Inc. 5000 Market Research Recruiting Firm)
- Founder, Human Layer AI — Practical AI + Human Operating Workflows
- Creator of ONE ASK AWAY™ & The Divergent Ask™ Methodology
- Entrepreneurs' Organization (EO) Leader & Keynote Speaker
- MIT Entrepreneurial Masters Program (EMP)
- Executive Education — Wharton & Harvard
Generate your Professional Ask and Personal Ask in 3 minutes—and let the AI Accountability Coach follow up with you via Email or WhatsApp.
Use The Scalable Ask™ and Divergent Ask™ tools to remove capacity bottlenecks and uncover hidden revenue inside your business.
Share your One Ask story, invite Jim to your podcast or conference, or inquire about an executive workshop.
Heard Jim Speak Tonight or Used The Ask Coach™? Leave a Comment or Takeaway
Share what ask this unlocked for you, your biggest takeaway from the session, or a note for Jim and fellow founders: