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Mar 1, 2016 · 26m · top-founders

How YoShirt App Went from $0-$1m Fast with Ben Williamson of YoShirt Episode 23

Ben Williamson · 14m spoken Nathan Latka · 9m 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 podcast, host Nathan Latka interviews YoShirt founder Ben Williamson to discuss his career under Steve Jobs at Apple and dissect the unit economics, mobile engineering, and venture funding behind his on-demand apparel startup.

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 38.7% of the talking time here. How this is scored →

Nathan as informed peer 5.0 Guest teaching 5.0 Guest disagreement 1.3 Nathan pushing back 2.0
05100:0010:0020:000:43–2:45 · Nathan as informed peer 3/10 Introducing Ben Williamson and Apple Career Highlights Latka warmly introduces Williamson and asks him to detail his background working under Steve Jobs at Apple. Williamson gives an overview of his decade-long tenure spanning retail growth, hardware, and software engineering without any tension.2:45–7:25 · Nathan as informed peer 4/10 Steve Jobs' Leadership Style and SWAT Team Execution Williamson explains how Steve Jobs utilized small SWAT teams of high-performing individuals to build products like iTunes, contrasting Apple's lean approach with conventional 50-person teams. Latka prompts with questions from their past conversation and summarizes the key takeaways.7:26–18:43 · Nathan as informed peer 6/10 YoShirt Mobile Platform, Production Process, and User Cases Latka presses into the exact metrics behind YoShirt, clarifying conversion rates, average order values, and gross margins. Williamson walks through the unit economics, cohort retention tracking, and the cut-and-sew manufacturing pipeline in detail.18:43–21:00 · Nathan as informed peer 7/10 Mid-Roll Promotion and Podcast Giveaway Announcement Following a mid-roll giveaway announcement, Latka executes rapid napkin math on YoShirt's total revenue based on previous numbers. Williamson confirms the baseline math is accurate and discloses their seed funding round.0:43–2:45 · Guest teaching 4/10 Introducing Ben Williamson and Apple Career Highlights Latka warmly introduces Williamson and asks him to detail his background working under Steve Jobs at Apple. Williamson gives an overview of his decade-long tenure spanning retail growth, hardware, and software engineering without any tension.2:45–7:25 · Guest teaching 6/10 Steve Jobs' Leadership Style and SWAT Team Execution Williamson explains how Steve Jobs utilized small SWAT teams of high-performing individuals to build products like iTunes, contrasting Apple's lean approach with conventional 50-person teams. Latka prompts with questions from their past conversation and summarizes the key takeaways.7:26–18:43 · Guest teaching 6/10 YoShirt Mobile Platform, Production Process, and User Cases Latka presses into the exact metrics behind YoShirt, clarifying conversion rates, average order values, and gross margins. Williamson walks through the unit economics, cohort retention tracking, and the cut-and-sew manufacturing pipeline in detail.18:43–21:00 · Guest teaching 4/10 Mid-Roll Promotion and Podcast Giveaway Announcement Following a mid-roll giveaway announcement, Latka executes rapid napkin math on YoShirt's total revenue based on previous numbers. Williamson confirms the baseline math is accurate and discloses their seed funding round.0:43–2:45 · Guest disagreement 1/10 Introducing Ben Williamson and Apple Career Highlights Latka warmly introduces Williamson and asks him to detail his background working under Steve Jobs at Apple. Williamson gives an overview of his decade-long tenure spanning retail growth, hardware, and software engineering without any tension.2:45–7:25 · Guest disagreement 1/10 Steve Jobs' Leadership Style and SWAT Team Execution Williamson explains how Steve Jobs utilized small SWAT teams of high-performing individuals to build products like iTunes, contrasting Apple's lean approach with conventional 50-person teams. Latka prompts with questions from their past conversation and summarizes the key takeaways.7:26–18:43 · Guest disagreement 2/10 YoShirt Mobile Platform, Production Process, and User Cases Latka presses into the exact metrics behind YoShirt, clarifying conversion rates, average order values, and gross margins. Williamson walks through the unit economics, cohort retention tracking, and the cut-and-sew manufacturing pipeline in detail.18:43–21:00 · Guest disagreement 1/10 Mid-Roll Promotion and Podcast Giveaway Announcement Following a mid-roll giveaway announcement, Latka executes rapid napkin math on YoShirt's total revenue based on previous numbers. Williamson confirms the baseline math is accurate and discloses their seed funding round.0:43–2:45 · Nathan pushing back 0/10 Introducing Ben Williamson and Apple Career Highlights Latka warmly introduces Williamson and asks him to detail his background working under Steve Jobs at Apple. Williamson gives an overview of his decade-long tenure spanning retail growth, hardware, and software engineering without any tension.2:45–7:25 · Nathan pushing back 1/10 Steve Jobs' Leadership Style and SWAT Team Execution Williamson explains how Steve Jobs utilized small SWAT teams of high-performing individuals to build products like iTunes, contrasting Apple's lean approach with conventional 50-person teams. Latka prompts with questions from their past conversation and summarizes the key takeaways.7:26–18:43 · Nathan pushing back 3/10 YoShirt Mobile Platform, Production Process, and User Cases Latka presses into the exact metrics behind YoShirt, clarifying conversion rates, average order values, and gross margins. Williamson walks through the unit economics, cohort retention tracking, and the cut-and-sew manufacturing pipeline in detail.18:43–21:00 · Nathan pushing back 4/10 Mid-Roll Promotion and Podcast Giveaway Announcement Following a mid-roll giveaway announcement, Latka executes rapid napkin math on YoShirt's total revenue based on previous numbers. Williamson confirms the baseline math is accurate and discloses their seed funding round.

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

0:00 · Nathan 51.5% · guest 48.5%0:00 · Nathan 51.5% · guest 48.5%3:00 · Nathan 25% · guest 75%3:00 · Nathan 25% · guest 75%6:00 · Nathan 27.7% · guest 72.3%6:00 · Nathan 27.7% · guest 72.3%9:00 · Nathan 43.6% · guest 56.4%9:00 · Nathan 43.6% · guest 56.4%12:00 · Nathan 18.1% · guest 81.9%12:00 · Nathan 18.1% · guest 81.9%15:00 · Nathan 32.9% · guest 67.1%15:00 · Nathan 32.9% · guest 67.1%18:00 · Nathan 61.7% · guest 38.3%18:00 · Nathan 61.7% · guest 38.3%21:00 · Nathan 30.3% · guest 69.7%21:00 · Nathan 30.3% · guest 69.7%24:00 · Nathan 68% · guest 32%24:00 · Nathan 68% · guest 32%
Sharpest disagreement ▶ 22:11 Defending Snapchat Product Design

When Latka bluntly labels Snapchat as poorly designed, Williamson directly contradicts him, arguing Latka is overlooking genuine product-market fit for younger demographics.

 Hardest push from Nathan ▶ 19:35 Demanding Financial Verification

Latka interrupts the interview flow to pin Williamson down on exact gross revenue figures derived from conversion and average order value metrics.

 Biggest teaching moment ▶ 4:35 Contrasting Apple's Lean Teams with Tech Industry Norms

Williamson reveals insider details on how Apple developed entire flagship applications like iTunes with just two engineers rather than typical 50-person corporate teams.

 Nathan holds their own ▶ 19:35 Latka's Rapid Financial Modeling

Latka demonstrates sharp business modeling expertise by calculating YoShirt's total historical gross margin and revenue from disjointed data points.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Ben Williamson and Apple Career Highlights 3410 Latka warmly introduces Williamson and asks him to detail his background working under Steve Jobs at Apple. Williamson gives an overview of his decade-long tenure spanning retail growth, hardware, and software engineering without any tension.
Steve Jobs' Leadership Style and SWAT Team Execution 4611 Williamson explains how Steve Jobs utilized small SWAT teams of high-performing individuals to build products like iTunes, contrasting Apple's lean approach with conventional 50-person teams. Latka prompts with questions from their past conversation and summarizes the key takeaways.
YoShirt Mobile Platform, Production Process, and User Cases 6623 Latka presses into the exact metrics behind YoShirt, clarifying conversion rates, average order values, and gross margins. Williamson walks through the unit economics, cohort retention tracking, and the cut-and-sew manufacturing pipeline in detail.
Mid-Roll Promotion and Podcast Giveaway Announcement 7414 Following a mid-roll giveaway announcement, Latka executes rapid napkin math on YoShirt's total revenue based on previous numbers. Williamson confirms the baseline math is accurate and discloses their seed funding round.

Statements from this episode (9)

Assertion Partly supported
Williamson: Apple's original iTunes application was built by two developers
“You know, if you look at like the original iTunes application, that was two guys.”
Ben Williamson Mar 1, 2016 ▶ 4:48
Assertion Not checkable as stated
Williamson: YoShirt has surpassed one million app downloads
“So we're north of a million downloads now.”
Ben Williamson Mar 1, 2016 ▶ 9:38
Assertion Not checkable as stated
Williamson: YoShirt achieves month-over-month double-digit percentage growth
“We've had double digit percentage growth really since we turned on the marketing engine and started any outbound marketing month over month.”
Ben Williamson Mar 1, 2016 ▶ 9:43
Assertion Not checkable as stated
Williamson: YoShirt's conversion rate is around two percent
“So it's over, you know, our conversion rate's about two percent right now, and we're actually in the process of going back and really instrumenting every single step and going back to the drawing board and looking at what's critical, what can we do to make the…”
Ben Williamson Mar 1, 2016 ▶ 10:54
Assertion Not checkable as stated
Williamson: YoShirt average order value is $38 to $42
“The majority are t-shirts, and the average purchase price, like, the average value per transaction is held steady. It's fluctuated between 38 and 42 dollars, so we're very consistent there.”
Ben Williamson Mar 1, 2016 ▶ 11:42
Assertion Not checkable as stated
Williamson: YoShirt achieves 60% gross margin on custom apparel
“So we have a 60% gross margin. Across the product. So we can produce a shirt, you know, if it's 40 bucks to your door, then, you know, let's say it's around, you know, 12 to 15 bucks for us to produce.”
Ben Williamson Mar 1, 2016 ▶ 14:25
Disclosure
Williamson: YoShirt Raised $1.125 Million in First Seed Round
“Yeah, we actually, so we did a release on the initial raise and I, yeah, so we raised one, two, five in the first seed.”
Ben Williamson Mar 1, 2016 ▶ 20:37
Opinion
Latka: Snapchat is probably the worst designed app I've ever seen
“Snapchat is Probably the shittiest designed app I've ever seen, yet it gets used so much.”
Nathan Latka Mar 1, 2016 ▶ 22:04
Opinion
Williamson: Snapchat UI has strong product-market fit for its core audience
“What I've realized about their product is that it speaks to the audience very, very well. If you watch a Use Snapchat. They know the app inside and out. And it's intuitive to them, but it's speaking to their customer. And it's not something, you know, that you…”
Ben Williamson Mar 1, 2016 ▶ 22:12
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