In this episode of The Inner Chief podcast, I speak to Jack Delosa, Founder and Chairman of The Entourage, on Frameworks for success, Building customer connection, and Raising capital from an investor’s viewpoint.

Jack is a successful entrepreneur, investor, and best-selling author, having founded The Entourage in 2010, Australia's largest business growth agency, through which he has helped clients generate over $6 billion in revenue.

Just 5 years’ prior, Jack had enrolled in a Commerce & Law Degree, only to drop out three months later to found a marketing agency in Melbourne.

Since then, he has been named on the Australian Financial Review's ‘Young Rich List' five times, and founded and invested in multiple businesses across diverse industries such as biotechnology and aviation.

Jack is the author of Unprofessional and Elevate and stars in the TV show Entrepreneurs, in which he shares insights from top business leaders.

In this CEO Masterclass we will share:

✅ Using frameworks to guide you to solving a unique problem in the market

✅ The benefits and pitfalls of raising capital versus bootstrapping your business

✅ The crucial role of both employee and customer feedback in continually refining your business operations, and

✅ The immense value of personal growth practices such as meditation for maintaining resilience and focus.

Connecting with Jack Delosa

You can connect with Jack via his website.

Books and resources

• We Who Wrestle with God: Perceptions of the Divine – by Jordan Peterson
• Books on Carl Jung – by James Hollis

Similar Episodes on customer journey

• Siobhan O’Sullivan, on Customer experience, looking at yourself in the mirror and how martial arts helped her accelerate her career
• Kevin Gaskell, on Transforming customer experience, driving extraordinary results, and daring to dream
• Jonathan Barouch, on Transforming Customer Experience with Technology and Culture 

“I think about how many layers there are of really intelligent, capable people. And I wonder how many of them have actually called the customer service line to gage the experience.”

On Early Career Lessons

• My childhood shaped my worldview as my parents ran Breaking the Cycle, a nonprofit helping at-risk youth, and I saw first-hand how business and impact could intertwine.
• I learned rebellion from the young people in our home. My parents always said, “Our favourite students are the scoundrels.” That stuck with me.
• I dropped out of university because I love learning. The system is structured to keep you in, not necessarily to develop you.
• My real education came from failure. I had four years of false starts – that was my apprenticeship.
• Every entrepreneur needs a fast feedback loop. It’s the only way to truly learn.
• His advice was whenever he met someone he thought how he could make them money, not how he could make money from them.

On Raising Capital vs Bootstrapping

• Raising capital is not a win – it’s when the hard work really begins, and now you have more pressure.
• Bootstrap for as long as possible. Too much capital too early can lull you into a false sense of security.
• Capital should be an accelerant. If you can’t turn $1M into $3M, you don’t need investment, you need a better business model.
• Focus on unit economics before expansion; don’t go fancy with international launches when the core isn’t solid.
• If your marketing is strong, you may never need to raise capital. Revenue should be your funding.

On Focus and Scaling a Business

• The hardest thing for anybody is a blank canvas, because you're essentially creating through trial and error. It's the hardest, longest and most expensive way to learn.
• “It worked so well, I stopped doing it.” The #1 mistake business owners make is chasing shiny objects.
• The fastest way to grow? Better → More → Different.
• Instead of looking sideways at new markets, look down: what are you already doing that you can do better?
• Business is a game of constraint management. Identify the biggest bottleneck and fix it before moving to the next.
• Customer journey is king. If you focus on every step of your customer’s experience, you can 10X your business without launching anything new.
• There's three rules to growth. Number one is focus. Number two is focus. And number three is focus.

On Brand and Value Proposition

• Brand isn’t a logo. It’s the sum of every customer touchpoint.
• If your Instagram is great but your customers are unhappy, your brand is broken.
• Executives lose touch because they don’t talk to customers. The best CEOs stay close to the frontline (see below).
• If you can’t articulate your value proposition in a sentence that makes sense to the customer, you don’t have one.
• People don’t buy what you do, they buy how it makes them feel. Your brand lives in that experience.

On Truly Understanding Your Customer

• The biggest risk for executives and corporations is distance from the customer. It’s the number one thing that will kill you.
• Too many leaders sit in fancy offices assuming what customers want, and then wonder why their product or service isn’t landing. 
• The quality of a business isn’t about how smart you sound in the boardroom, it’s about what actually happens at the frontline.
• If you’re not talking to customers regularly, you’re flying blind. Get out there, listen, and engage with real feedback.
• Before you launch something new, don’t ask, “Is this a good idea?” Ask, “Is this solving a real problem for a hungry audience?”

On Mastery and Excellence

• Mastery isn’t exciting; it’s the relentless pursuit of better, better, better.
• The hardest thing in business? True excellence. It’s not easy, which is why it’s rare and valuable.
• People crave progress, which is why they abandon mastery too soon. The reality? Progress slows as you level up.
• If you need constant excitement to stay motivated, you’ll quit before you get great.
• The best in the world keep going when it’s boring, when it’s tough, and when no one’s watching.

Final message of wisdom and hope for future leaders

• There are no silver bullets.
• Better, then more, then different.

Stay epic,

Greg