Today, Jon and Kory discuss the moments that define careers. The ones where you have to leap before you know exactly how things will turn out.

From leaving secure jobs to betting on yourself, they reflect on the decisions that shaped their own careers and why waiting until you feel "ready" is often the biggest barrier to growth. They explore the importance of having a strong support network, embracing discomfort, and accepting that sometimes you need to take a step backwards before you can move forwards.

This is an honest conversation about risk, resilience, and why the biggest opportunities often sit just outside your comfort zone.

Timestamps

00:00 - Start
00:35 - Taking a giant leap
01:28 - A moment Kory took a giant leap
04:51 - Taking the leap before you feel ready
06:46 - Why Jon made the giant leap to go full time on the podcast
08:45 - The importance of a support network
10:10 - Get comfortable being uncomfortable
14:50 - The risks of taking the leap of faith
19:02 - Sometimes you have to take a step back to take a step forward
22:01 - Are you willing to lose the battle to win the war?
24:42 - You need a high risk tolerance

Jon and Kory explore why human connection matters more than ever in a world increasingly dominated by screens, automation, and AI.

From the power of in-person experiences to the importance of empathy in business, they discuss why relationships are still the foundation of great leadership, marketing, and culture. Jon explains why he only records podcasts face-to-face, Kory shares why B2B is ultimately human-to-human, and together they unpack the mistakes agencies often make by forgetting the people behind the pitch.

Timestamps

00:00 - Start
01:42 - What do we mean by human to human?
05:11 - Why we need more humanity now
06:55 - Why Jon only does podcasts in person
09:56 - What the data says about being in person
11:25 - The power of an in person experience
16:03 - Why experience matters
18:58 - Why being human matters in B2B
22:38 - Human relationships and the impact they can have
25:21 - What every agency gets wrong in a pitch
25:54 - How to be more human
27:33 - Everyone has something going on

Today Jon and Kory explore the surprising link between leadership and exercise. From CEOs and founders to top marketers, many high performers share one habit in common: they make time to move.

The duo discuss why working out often feels selfish (when it shouldn't), how to maintain healthy habits while travelling, and what companies can do to encourage their teams to prioritise wellbeing. Jon also breaks down his philosophy of running, explaining how different stages of a workout mirror the rhythms of work and life.

This is a conversation about energy, discipline, and why taking care of yourself might be one of the most important leadership skills of all.

Timestamps

00:00 - Start
00:47 - The common thread for successful people
02:37 - Feeling guilty for working out
03:40 - How to workout while on the road
05:08 - How employees can encourage their employees to workout
09:31 - Mile 1: The hard part
11:37 - Mile 2: Rhythm
12:59 - Mile 3: Harmony
14:35 - Mile 4: Acceleration
17:36 - Mile 5: Let it rip
18:30 - How important is music to working out
19:55 - Becoming at one with the run
20:40 - Break things down into parts
23:06 - The two mountains