StarZero All shows Try the podcast clipper →

Mar 3, 2016 · 23m · top-founders

The Confident Way to Quit Your Corporate Job with Greg Hickman

Greg Hickman · 14m spoken Nathan Latka · 6m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Top, host Nathan Latka interviews entrepreneur Greg Hickman on his calculated transition from corporate leadership to launching a digital agency, detailing his financial preparation, agency pricing models, and strategic pivot toward marketing automation.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 32.4% of the talking time here. How this is scored →

Nathan as informed peer 3.8 Guest teaching 3.0 Guest disagreement 1.2 Nathan pushing back 2.4
05100:0010:0020:001:55–6:28 · Nathan as informed peer 4/10 Strategy and Metrics for Leaving Corporate Employment Latka explores Hickman's transition from Cabela's to entrepreneurship, pressing for exact numbers regarding compensation and savings thresholds. Latka effectively synthesizes Hickman's rule of hitting 60% of corporate salary before resigning.6:28–10:04 · Nathan as informed peer 4/10 Service Packaging, Pricing Models, and Reaching $6K MRR Latka pushes Hickman on precise client counts when Hickman uses vague phrasing like 'a couple'. Hickman explains the economics of selling a $1,500 upfront audit roadmap to convert hesitant monthly retainer clients.10:04–12:35 · Nathan as informed peer 3/10 Managing Client Churn and Understanding Retention Pitfalls Latka asks Hickman about emotional resilience and root causes behind losing $1,300 in MRR in a single day. Hickman educates the audience on mobile marketing churn dynamics, explaining the reliance on client opt-in list building.12:35–16:53 · Nathan as informed peer 4/10 Strategic Pivot to Infusionsoft Marketing Automation Services Hickman gently clarifies that he is testing a beta rather than having executed a full pivot. He explains why selling Infusionsoft automation solves an immediate recognized pain, unlike educating SMBs on mobile marketing.16:55–21:33 · Nathan as informed peer 4/10 Mid-Show Promo and GoPro Giveaway Announcement Latka conducts his signature Famous Five rapid-fire questions, dropping names of upcoming guests and elaborating on Hickman's advice to fall in love with the problem rather than the solution.1:55–6:28 · Guest teaching 2/10 Strategy and Metrics for Leaving Corporate Employment Latka explores Hickman's transition from Cabela's to entrepreneurship, pressing for exact numbers regarding compensation and savings thresholds. Latka effectively synthesizes Hickman's rule of hitting 60% of corporate salary before resigning.6:28–10:04 · Guest teaching 3/10 Service Packaging, Pricing Models, and Reaching $6K MRR Latka pushes Hickman on precise client counts when Hickman uses vague phrasing like 'a couple'. Hickman explains the economics of selling a $1,500 upfront audit roadmap to convert hesitant monthly retainer clients.10:04–12:35 · Guest teaching 4/10 Managing Client Churn and Understanding Retention Pitfalls Latka asks Hickman about emotional resilience and root causes behind losing $1,300 in MRR in a single day. Hickman educates the audience on mobile marketing churn dynamics, explaining the reliance on client opt-in list building.12:35–16:53 · Guest teaching 4/10 Strategic Pivot to Infusionsoft Marketing Automation Services Hickman gently clarifies that he is testing a beta rather than having executed a full pivot. He explains why selling Infusionsoft automation solves an immediate recognized pain, unlike educating SMBs on mobile marketing.16:55–21:33 · Guest teaching 2/10 Mid-Show Promo and GoPro Giveaway Announcement Latka conducts his signature Famous Five rapid-fire questions, dropping names of upcoming guests and elaborating on Hickman's advice to fall in love with the problem rather than the solution.1:55–6:28 · Guest disagreement 1/10 Strategy and Metrics for Leaving Corporate Employment Latka explores Hickman's transition from Cabela's to entrepreneurship, pressing for exact numbers regarding compensation and savings thresholds. Latka effectively synthesizes Hickman's rule of hitting 60% of corporate salary before resigning.6:28–10:04 · Guest disagreement 1/10 Service Packaging, Pricing Models, and Reaching $6K MRR Latka pushes Hickman on precise client counts when Hickman uses vague phrasing like 'a couple'. Hickman explains the economics of selling a $1,500 upfront audit roadmap to convert hesitant monthly retainer clients.10:04–12:35 · Guest disagreement 1/10 Managing Client Churn and Understanding Retention Pitfalls Latka asks Hickman about emotional resilience and root causes behind losing $1,300 in MRR in a single day. Hickman educates the audience on mobile marketing churn dynamics, explaining the reliance on client opt-in list building.12:35–16:53 · Guest disagreement 2/10 Strategic Pivot to Infusionsoft Marketing Automation Services Hickman gently clarifies that he is testing a beta rather than having executed a full pivot. He explains why selling Infusionsoft automation solves an immediate recognized pain, unlike educating SMBs on mobile marketing.16:55–21:33 · Guest disagreement 1/10 Mid-Show Promo and GoPro Giveaway Announcement Latka conducts his signature Famous Five rapid-fire questions, dropping names of upcoming guests and elaborating on Hickman's advice to fall in love with the problem rather than the solution.1:55–6:28 · Nathan pushing back 2/10 Strategy and Metrics for Leaving Corporate Employment Latka explores Hickman's transition from Cabela's to entrepreneurship, pressing for exact numbers regarding compensation and savings thresholds. Latka effectively synthesizes Hickman's rule of hitting 60% of corporate salary before resigning.6:28–10:04 · Nathan pushing back 3/10 Service Packaging, Pricing Models, and Reaching $6K MRR Latka pushes Hickman on precise client counts when Hickman uses vague phrasing like 'a couple'. Hickman explains the economics of selling a $1,500 upfront audit roadmap to convert hesitant monthly retainer clients.10:04–12:35 · Nathan pushing back 2/10 Managing Client Churn and Understanding Retention Pitfalls Latka asks Hickman about emotional resilience and root causes behind losing $1,300 in MRR in a single day. Hickman educates the audience on mobile marketing churn dynamics, explaining the reliance on client opt-in list building.12:35–16:53 · Nathan pushing back 3/10 Strategic Pivot to Infusionsoft Marketing Automation Services Hickman gently clarifies that he is testing a beta rather than having executed a full pivot. He explains why selling Infusionsoft automation solves an immediate recognized pain, unlike educating SMBs on mobile marketing.16:55–21:33 · Nathan pushing back 2/10 Mid-Show Promo and GoPro Giveaway Announcement Latka conducts his signature Famous Five rapid-fire questions, dropping names of upcoming guests and elaborating on Hickman's advice to fall in love with the problem rather than the solution.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 65.2% · guest 34.8%0:00 · Nathan 65.2% · guest 34.8%3:00 · Nathan 18.7% · guest 81.3%3:00 · Nathan 18.7% · guest 81.3%6:00 · Nathan 5.2% · guest 94.8%6:00 · Nathan 5.2% · guest 94.8%9:00 · Nathan 10% · guest 90%9:00 · Nathan 10% · guest 90%12:00 · Nathan 16.2% · guest 83.8%12:00 · Nathan 16.2% · guest 83.8%15:00 · Nathan 57% · guest 43%15:00 · Nathan 57% · guest 43%18:00 · Nathan 44% · guest 56%18:00 · Nathan 44% · guest 56%21:00 · Nathan 48.9% · guest 51.1%21:00 · Nathan 48.9% · guest 51.1%
Sharpest disagreement ▶ 12:38 Clarifying pivot status

Hickman mildly pushes back on Latka's statement that he had already fully pivoted, clarifying that he is merely exploring the transition via a beta program.

 Hardest push from Nathan ▶ 7:30 Pressing on vague numbers

Latka immediately interrupts Hickman's narrative to demand exact numbers after Hickman uses the vague phrase 'a couple'.

 Biggest teaching moment ▶ 13:42 The friction of creating demand vs solving existing pain

Hickman educates Latka on the fatal sales flaw of his first agency: spending excessive time educating SMBs on problems they did not realize they had.

 Nathan holds their own ▶ 5:11 Formulating the side-hustle exit rule

Latka extracts and sharpens Hickman's rambling answer into a clean, actionable financial benchmark formula for the audience.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Strategy and Metrics for Leaving Corporate Employment 4212 Latka explores Hickman's transition from Cabela's to entrepreneurship, pressing for exact numbers regarding compensation and savings thresholds. Latka effectively synthesizes Hickman's rule of hitting 60% of corporate salary before resigning.
Service Packaging, Pricing Models, and Reaching $6K MRR 4313 Latka pushes Hickman on precise client counts when Hickman uses vague phrasing like 'a couple'. Hickman explains the economics of selling a $1,500 upfront audit roadmap to convert hesitant monthly retainer clients.
Managing Client Churn and Understanding Retention Pitfalls 3412 Latka asks Hickman about emotional resilience and root causes behind losing $1,300 in MRR in a single day. Hickman educates the audience on mobile marketing churn dynamics, explaining the reliance on client opt-in list building.
Strategic Pivot to Infusionsoft Marketing Automation Services 4423 Hickman gently clarifies that he is testing a beta rather than having executed a full pivot. He explains why selling Infusionsoft automation solves an immediate recognized pain, unlike educating SMBs on mobile marketing.
Mid-Show Promo and GoPro Giveaway Announcement 4212 Latka conducts his signature Famous Five rapid-fire questions, dropping names of upcoming guests and elaborating on Hickman's advice to fall in love with the problem rather than the solution.

Statements from this episode (6)

Disclosure
Hickman paid $25k debt and replaced 60% of salary before quitting
“And I, my goal was to get to, I kind of had three requirements for what I needed to, in order to take the quote unquote leap. And it was to have paid off my debt, which at the time, Was about 25 K in debt to be making at least 60% of my full-time salary throug…”
Greg Hickman Mar 3, 2016 ▶ 4:22
Disclosure
Hickman: Earned low six figures as Head of Mobile at Cabela's
“So at Cabela's it was just low six figures, like just over a hundred. After bonuses.”
Greg Hickman Mar 3, 2016 ▶ 4:53
Assertion Not checkable as stated
Hickman: Mobile Marketing Engine peaked at just over $6,000 MRR
“The highest MRR that we had was, and I've been focused on MRR. You know, we did some of these one-off obviously discovery processes and everything. The MRR got to just over six grand.”
Greg Hickman Mar 3, 2016 ▶ 9:27
Assertion Not checkable as stated
Hickman: Mobile Marketing Engine lost $1,300 in MRR in one month
“So we hit six grand. 30 days later, we lost two of our early, early clients that were like the early clients that were paying at the five, two clients at the 500 mark and one at like the three 50 mark. So we lost like 1300 dollars right at like All in one mont…”
Greg Hickman Mar 3, 2016 ▶ 9:42
Insight
Hickman: Pitching unrecognized pain points creates an arduous B2B sales cycle
“The biggest thing that I found the challenge is that they don't they don't yet understand mobile and they don't even think that they have a problem. So like, if there's no pain, I'm coming in trying to show them that there's a pain, then educate them on mobile…”
Greg Hickman Mar 3, 2016 ▶ 13:43
Assertion Not checkable as stated
Hickman signed first marketing automation customer within seven days of idea
“We had the first customer sign on today, and, you know, this idea came last week, so not even seven days ago. The first paying customer, and I have two customers that are basically about to be signing on as well”
Greg Hickman Mar 3, 2016 ▶ 16:34
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more