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Mar 4, 2016 · 18m · top-founders

Startup COO Leaves after 500 Accelerator, Left with 1% Equity with Jules Hill Episode 183

Jules Hill · 9m spoken Nathan Latka · 6m spoken
0:00 / 0:00

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Host Nathan Latka interviews former Cellbreaker COO Jules Hill to examine the realities of early-stage startups, including surviving on minimal salary, navigating the 500 Startups accelerator, and managing equity vesting upon departure.

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 39.9% of the talking time here. How this is scored →

Nathan as informed peer 3.4 Guest teaching 1.4 Guest disagreement 1.2 Nathan pushing back 2.2
05100:0010:001:06–4:28 · Nathan as informed peer 3/10 Introducing Jules Hill and His Early Entrepreneurial Journey Nathan introduces Jules and probes into his early career decisions, asking how he evaluated joining a startup with minimal cash over high-paying Wall Street and consulting offers. Jules cooperatively details his risk-reward calculation and low starting salary.4:30–7:58 · Nathan as informed peer 3/10 500 Startups Accelerator and Side Hustle Survival Strategy Nathan drills into Jules's financial survival strategy while taking reduced startup pay during 500 Startups. Jules explains his diversified income streams including USMC reserve duty, freelance graphic design, and renting rooms.8:00–11:42 · Nathan as informed peer 6/10 Departing Cellbreaker Amidst Legal Friction and Equity Vesting Nathan investigates why Jules left Cellbreaker and presses on the equity outcome after learning Jules only retained about 1% of his initial 6%. Nathan demonstrates his understanding of standard startup equity vesting schedules and cliffs for the audience.11:42–14:36 · Nathan as informed peer 3/10 Transitioning to Windsor Circle as First Analytics Manager Nathan inquires about Jules's new role at Windsor Circle, including funding and compensation. Jules firmly sets a boundary refusing to disclose funding amounts due to being new at the company, which Nathan respects.14:40–17:51 · Nathan as informed peer 2/10 Famous Five Rapid-Fire Questions and Career Advice The conversation moves through the standard rapid-fire Famous Five routine with relaxed, collaborative answers regarding tools, habits, and career reflections.1:06–4:28 · Guest teaching 1/10 Introducing Jules Hill and His Early Entrepreneurial Journey Nathan introduces Jules and probes into his early career decisions, asking how he evaluated joining a startup with minimal cash over high-paying Wall Street and consulting offers. Jules cooperatively details his risk-reward calculation and low starting salary.4:30–7:58 · Guest teaching 2/10 500 Startups Accelerator and Side Hustle Survival Strategy Nathan drills into Jules's financial survival strategy while taking reduced startup pay during 500 Startups. Jules explains his diversified income streams including USMC reserve duty, freelance graphic design, and renting rooms.8:00–11:42 · Guest teaching 2/10 Departing Cellbreaker Amidst Legal Friction and Equity Vesting Nathan investigates why Jules left Cellbreaker and presses on the equity outcome after learning Jules only retained about 1% of his initial 6%. Nathan demonstrates his understanding of standard startup equity vesting schedules and cliffs for the audience.11:42–14:36 · Guest teaching 1/10 Transitioning to Windsor Circle as First Analytics Manager Nathan inquires about Jules's new role at Windsor Circle, including funding and compensation. Jules firmly sets a boundary refusing to disclose funding amounts due to being new at the company, which Nathan respects.14:40–17:51 · Guest teaching 1/10 Famous Five Rapid-Fire Questions and Career Advice The conversation moves through the standard rapid-fire Famous Five routine with relaxed, collaborative answers regarding tools, habits, and career reflections.1:06–4:28 · Guest disagreement 1/10 Introducing Jules Hill and His Early Entrepreneurial Journey Nathan introduces Jules and probes into his early career decisions, asking how he evaluated joining a startup with minimal cash over high-paying Wall Street and consulting offers. Jules cooperatively details his risk-reward calculation and low starting salary.4:30–7:58 · Guest disagreement 1/10 500 Startups Accelerator and Side Hustle Survival Strategy Nathan drills into Jules's financial survival strategy while taking reduced startup pay during 500 Startups. Jules explains his diversified income streams including USMC reserve duty, freelance graphic design, and renting rooms.8:00–11:42 · Guest disagreement 2/10 Departing Cellbreaker Amidst Legal Friction and Equity Vesting Nathan investigates why Jules left Cellbreaker and presses on the equity outcome after learning Jules only retained about 1% of his initial 6%. Nathan demonstrates his understanding of standard startup equity vesting schedules and cliffs for the audience.11:42–14:36 · Guest disagreement 2/10 Transitioning to Windsor Circle as First Analytics Manager Nathan inquires about Jules's new role at Windsor Circle, including funding and compensation. Jules firmly sets a boundary refusing to disclose funding amounts due to being new at the company, which Nathan respects.14:40–17:51 · Guest disagreement 0/10 Famous Five Rapid-Fire Questions and Career Advice The conversation moves through the standard rapid-fire Famous Five routine with relaxed, collaborative answers regarding tools, habits, and career reflections.1:06–4:28 · Nathan pushing back 2/10 Introducing Jules Hill and His Early Entrepreneurial Journey Nathan introduces Jules and probes into his early career decisions, asking how he evaluated joining a startup with minimal cash over high-paying Wall Street and consulting offers. Jules cooperatively details his risk-reward calculation and low starting salary.4:30–7:58 · Nathan pushing back 2/10 500 Startups Accelerator and Side Hustle Survival Strategy Nathan drills into Jules's financial survival strategy while taking reduced startup pay during 500 Startups. Jules explains his diversified income streams including USMC reserve duty, freelance graphic design, and renting rooms.8:00–11:42 · Nathan pushing back 4/10 Departing Cellbreaker Amidst Legal Friction and Equity Vesting Nathan investigates why Jules left Cellbreaker and presses on the equity outcome after learning Jules only retained about 1% of his initial 6%. Nathan demonstrates his understanding of standard startup equity vesting schedules and cliffs for the audience.11:42–14:36 · Nathan pushing back 2/10 Transitioning to Windsor Circle as First Analytics Manager Nathan inquires about Jules's new role at Windsor Circle, including funding and compensation. Jules firmly sets a boundary refusing to disclose funding amounts due to being new at the company, which Nathan respects.14:40–17:51 · Nathan pushing back 1/10 Famous Five Rapid-Fire Questions and Career Advice The conversation moves through the standard rapid-fire Famous Five routine with relaxed, collaborative answers regarding tools, habits, and career reflections.

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

0:00 · Nathan 65.7% · guest 34.3%0:00 · Nathan 65.7% · guest 34.3%3:00 · Nathan 24.8% · guest 75.2%3:00 · Nathan 24.8% · guest 75.2%6:00 · Nathan 36.8% · guest 63.2%6:00 · Nathan 36.8% · guest 63.2%9:00 · Nathan 25.9% · guest 74.1%9:00 · Nathan 25.9% · guest 74.1%12:00 · Nathan 28.4% · guest 71.6%12:00 · Nathan 28.4% · guest 71.6%15:00 · Nathan 51.5% · guest 48.5%15:00 · Nathan 51.5% · guest 48.5%18:00 · Nathan 100% · guest 0%18:00 · Nathan 100% · guest 0%
Sharpest disagreement ▶ 12:51 Jules refuses to comment on company funding

When Nathan presses on how much venture capital Windsor Circle has raised, Jules clearly establishes a boundary and refuses to answer.

 Hardest push from Nathan ▶ 11:01 Nathan challenges the 1% equity retention

Nathan interrupts with surprise upon hearing Jules only walked away with 1%, pressing to understand how the original 6% allocation diminished.

 Biggest teaching moment ▶ 6:16 Jules explains bootstrapping personal runway

Jules breaks down how stacking USMC reserve pay, real estate house-hacking, and freelance design work enabled him to survive on a low startup salary.

 Nathan holds their own ▶ 11:10 Nathan explains startup vesting schedules and cliffs

Nathan demonstrates his domain expertise by contextualizing Jules's equity loss with an explanation of standard 4-year vesting schedules and 1-year cliffs.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Jules Hill and His Early Entrepreneurial Journey 3112 Nathan introduces Jules and probes into his early career decisions, asking how he evaluated joining a startup with minimal cash over high-paying Wall Street and consulting offers. Jules cooperatively details his risk-reward calculation and low starting salary.
500 Startups Accelerator and Side Hustle Survival Strategy 3212 Nathan drills into Jules's financial survival strategy while taking reduced startup pay during 500 Startups. Jules explains his diversified income streams including USMC reserve duty, freelance graphic design, and renting rooms.
Departing Cellbreaker Amidst Legal Friction and Equity Vesting 6224 Nathan investigates why Jules left Cellbreaker and presses on the equity outcome after learning Jules only retained about 1% of his initial 6%. Nathan demonstrates his understanding of standard startup equity vesting schedules and cliffs for the audience.
Transitioning to Windsor Circle as First Analytics Manager 3122 Nathan inquires about Jules's new role at Windsor Circle, including funding and compensation. Jules firmly sets a boundary refusing to disclose funding amounts due to being new at the company, which Nathan respects.
Famous Five Rapid-Fire Questions and Career Advice 2101 The conversation moves through the standard rapid-fire Famous Five routine with relaxed, collaborative answers regarding tools, habits, and career reflections.

Statements from this episode (7)

Assertion Not checkable as stated
Hill: Cellbreaker had raised about $50K when he joined
“Cellbreaker had raised about 50 K when I... Decided to kind of join full time.”
Jules Hill Mar 4, 2016 ▶ 1:50
Disclosure
Hill: Started with around $20,000 a year salary at Cellbreaker
“I started off with around 20,000 a year.”
Jules Hill Mar 4, 2016 ▶ 3:48
Disclosure
Jules Hill joined Cellbreaker with 6% equity and milestone-based compensation reviews
“We, I came on initially at six percent with the option to sort of, as the time went on, we had sort of set milestones for us to reach at which point I would be offered more or an increase in salary, basically open to discussion.”
Jules Hill Mar 4, 2016 ▶ 4:39
Assertion Supported
Hill: Cellbreaker joined 500 Startups and received a $100K investment
“One of the big sort of milestones we reached was getting accepted into the 500 startups program out in California. That comes with a hundred K investment as well.”
Jules Hill Mar 4, 2016 ▶ 5:02
Assertion Not checkable as stated
Jules Hill: Cellbreaker failed to hit aggressive internal growth milestones
“We didn't hit the milestones that I had expected. I had set some pretty aggressive milestones. We didn't hit them.”
Jules Hill Mar 4, 2016 ▶ 8:30
Disclosure
Jules Hill: Cellbreaker engaged in carrier partnership and M&A talks
“We were talking with cell phone carriers. We were talking with partners about, you know mergers, acquisitions, that kind of stuff. We're talking with investors”
Jules Hill Mar 4, 2016 ▶ 9:46
Disclosure
Jules Hill retained roughly 1% equity in Cellbreaker upon his departure
“I, yeah, well, I guess I still have about one percent, I think is roughly what I have, if I recall correctly.”
Jules Hill Mar 4, 2016 ▶ 10:50
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