Ep 191 - "Rabbit Trails: The Last 60 Days"

Dec 23, 2025

Dive into a candid discussion about the whirlwind of the past 60 days managing two fast-growing companies. The hosts share insights on battling negative momentum and the critical need to celebrate wins, even during exhaustion. They explore how pressure can erode routines, the challenges of constant context-shifting, and the paradox of feeling both drained yet fulfilled. Plus, discover unique techniques like fasting and the potential of psychedelic therapy as tools for emotional resets.

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INSIGHT

Streaks Of Negative Momentum Matter

Chris and Brennan describe a 60-day stretch of negative momentum that they worked to stop rather than immediately convert to growth.
Small signs of stabilization mattered more than instant wins during that recovery period.

ADVICE

Celebrate Small Wins Intentionally

Celebrate wins intentionally because skipping celebration fuels long-term burnout for founders and teams.
Pause and name successes even when exhausted to preserve energy and morale.

INSIGHT

Hold Conflicting Truths Simultaneously

Two truths can coexist: investments that underperformed and confidence in future opportunities.
Holding both perspectives helps leaders remain realistic and bullish simultaneously.

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In this episode of Head, Heart, and Boots, Brandon and I sit down for a raw, unfiltered look at the last 60 days - the travel, the pressure, the wins we haven’t slowed down to celebrate, and the realities of running two fast-moving companies at the same time. We talk about what it feels like when your business hits a streak of negative momentum, how long it takes to turn the ship, and why even small signs of stabilization matter more than you think.

We get into the personal side, too - the exhaustion of constant context-shifting, how hard it’s been to hold routines together, and what we’re learning about rest, recovery, and leadership when everything speeds up at once. From supporting two teams across time zones, to protecting focus, to the conversations that are shaping our 2026 planning, this is a behind-the-scenes look at the real rhythms of entrepreneurship.

Hope you enjoy.

Chris

Why You Should Listen

[00:01:20] What the last 60 days looked like inside two growing companies - and how to recognize when negative momentum starts, stops, and finally stabilizes

[00:03:49] Why celebrating wins matters (even when you’re exhausted) and how missing those moments creates long-term burnout for founders and teams

[00:07:26] The truth about routines under pressure - how travel, growth, and leadership demands quietly erode the habits that keep you grounded

[00:24:13] How “context shifting” destroys focus, drains leaders, and impacts entire organizations - and why reducing it may be the key to a healthier 2026

[00:38:47] A candid look at stress, mental resets, and the tools leaders are turning to - from saunas to silence to psychedelic therapy

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