Milestone Episode 300 is a behind the scenes centennial conversation with Shelby Hobbs, recorded right in the messy middle of real life. Kelly and Shelby hit record in the narrow window before the kids get home, with a baby sleeping nearby, a toddler napping upstairs, and the daily marathon happening in real time, because that’s genuinely how the show and the household get built.

From there, the episode becomes a reflection on what 300 episodes actually means: the gratitude, the growth, and the belief that this milestone is the start of the next phase, not the finish line. Kelly thanks the listeners for riding with him through year three, celebrates winning a Signal Award, and sets the tone for 2026 as “our year” while Shelby echoes that momentum and the bigger “new era” feeling they’re sensing personally and globally.

Key Takeaways:

1. Progress gets built in the in between moments, not perfect schedules, so show up anyway and hit record when you can.

2. Consistency compounds, and 300 episodes is proof that long games create massive outcomes.

3. Treat milestones like a launchpad, not a finish line, because 300 is the start of the next phase and 2026 is the push forward.

4. Gratitude is a practice, not a hindsight review, and you can train yourself to actually notice when life is good right now.

5. Your time horizon changes everything, because one year can feel frustrating but five years will shock you with what you have built.

6. When motivation feels heavy, aim for inspiration, and let your future self pull you forward instead of pressure pushing you.

7. Community is not optional, because the best opportunities usually come through people who open doors for you, not you grinding alone.

8. The right room changes everything, and Catalyst Club was born by watching real connections and collaboration happen inside the Accelerator.

9. Do not box yourself into local only thinking, virtual community can be just as real and even more powerful because of global perspectives.

10. Trust your gut, stay open to the unexpected, and keep upgrading your skills and tools, because opportunity shows up fast when you are ready to say yes.

If Episode 300 hit you in the chest, it is because you can feel it too. 300 is the start of the next phase and 2026 is our year. The Catalyst Club exists for that exact moment when you stop waiting for the “right time” and you decide to build anyway, in the in between moments, with real life happening around you. This is the room for founders, business developers, and next generation leaders who want real connection, real support, and real momentum in the year that you finally make the leap.

Inside Catalyst Club there is no hierarchy, no posturing, and no competition for power. It is leaders supporting leaders, showing up as humans, leaving ego at the door, and actually sharing what is real. It is also fully virtual, which means the community is happening every day with members from around the world and perspectives you cannot get in a local only box. If you are ready to step into the new era we talked about and make 2026 the year you stop circling the runway, come join us here: www.kellykennedyofficial.com/thecatalystclub

In this very special episode of The Business Development Podcast, Kelly Kennedy sits down with Jake Gold, one of the most influential architects of Canadian music and the longtime manager behind The Tragically Hip. Jake takes listeners behind the curtain on what a music manager actually does, not as a hype man, but as the CEO of a complex business where touring, deals, team decisions, merchandising, data, and long term career strategy all run through one leader. He shares the moment he first saw The Tragically Hip live and knew instantly they had to be signed, plus how conviction, detail obsession, and a willingness to say no are what separate career building from chasing quick wins.

This conversation is packed with crossover lessons for founders, CEOs, and business developers, especially around standards, positioning, and being relentlessly curious as the market changes. Jake breaks down why the music industry is bigger than ever, why direct to consumer and data matter, and why the barrier to entry being low does not change the one truth that decides everything: you still have to be great. Kelly also acknowledges the human side of legacy, including the grief the country felt around Gord Downie, and Jake shares how he stays grounded and sustainable across decades in a 24/7 industry, while hinting at meaningful plans ahead for what comes next.

Key Takeaways:

1. You will know greatness when you feel it and it is an involuntary response, not a logical checklist.

2. Great careers are built by setting the real bar and realizing what “next level” actually looks like the first time you witness it.

3. A great manager is basically the CEO of the band’s company, overseeing every revenue stream, cost, and decision with the artists as the board.

4. Sustainable performance comes from ruthless time protection: knowing when not to get involved, saying no, and avoiding time wasters.

5. If you do not believe in what you represent, you will eventually get bored and move on, so belief is the fuel of long term excellence.

6. The small stuff is the big stuff: details matter because this is the whole business and you do not get paid unless it works.

7. There is no plan B if you want career level outcomes, and if the artist or founder loses belief, the manager cannot save it.

8. Curiosity is a competitive advantage: keep learning, keep reading, and bring new ideas to the table even when you are the most experienced person in the room.

9. Data and direct fan connection are core now, and the winners will understand audiences, demographics, and DTC relationships better than ever.

10. In a world where anyone can publish, the filter is still the same: you have to be great, the cream rises, and longevity is the real proof.

Connect with Jake Gold and learn more about his work:

The Management Trust (Official Site)

https://mgmtrust.ca/

Jake Gold on LinkedIn

https://www.linkedin.com/in/jake-gold-92046030/

If you know you are built for more, you belong in The Catalyst Club. It is a private, high trust community for founders, business developers, and next generation leaders who want real connection, real support, and real momentum.

Join us today: https://www.kellykennedyofficial.com/thecatalystclub

Episode 298 features Jake Karls, co founder and chief rainmaker of Mid Day Squares, breaking down how a kitchen table idea turned into a multimillion dollar brand by winning attention the hard way, through relentless storytelling and real human connection. He explains why attention is one of the most valuable assets in business, why you cannot buy trust with generic marketing, and why your story is the one advantage competitors cannot copy, if you are willing to share the good and the ugly.

The conversation also goes deep on the cost of building at full speed. Jake opens up about burnout in a way most founders never do, from chronic fatigue and brain fog to spiraling anxiety and feeling completely out of control, and how stepping away, therapy, and real recovery practices helped him rebuild. It is a powerful reminder that growth is a long game, and the strongest leaders are the ones who protect their health while they keep showing up.

Key Takeaways:

1. Attention is one of the most valuable assets now, and you have to earn it, not just pay for it.

2. People do not connect to product claims, they connect to emotion, meaning, and a story that feels real.

3. Your story is the one advantage competitors cannot copy, so treat it like an asset and share it on purpose.

4. Trust is built by showing the good and the ugly, not by trying to look perfect.

5. Impostor syndrome gets louder when you perform for approval instead of showing up as yourself.

6. Comparison is only useful if it inspires you, otherwise it quietly poisons your energy and progress.

7. Overworking for too long is not toughness, stepping back can be the move that lets you go ten steps forward.

8. Therapy is not a crisis move, it is leadership work that strengthens communication, perspective, and resilience.

9. Your business cannot be your identity, because that pressure will break you when life hits.

10. Surround yourself with real people who want you to win, and talk about the hard stuff before it turns into chaos.

Follow Jake Karl's on LinkedIn

Check out Mid-Day Squares

If you love this show, you will love The Catalyst Club. It is where founders and leaders take these conversations off the podcast and into real rooms, real relationships, and real support that helps you move faster and lead stronger.

Join us today www.kellykennedyofficial.com/thecatalystclub