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Jun 10, 2016 · 23m · top-founders

This App is Redefining On Demand Apparel Commerce with 3m Downlaods and $3m+ In Sales, EP 273: Ben Williamson

Ben Williamson · 11m 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

Host Nathan Latka interviews Yo Shirt founder and Apple veteran Ben Williamson to explore how the mobile commerce platform achieved three million downloads and $3 million in revenue through on-demand apparel manufacturing and creative brand partnerships.

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 47.2% of the talking time here. How this is scored →

Nathan as informed peer 3.9 Guest teaching 2.7 Guest disagreement 0.7 Nathan pushing back 1.8
05100:0010:0020:000:43–4:02 · Nathan as informed peer 6/10 Top Tribe Weekly Giveaway and Winner Announcement After opening housekeeping and intro, Nathan quickly presses Ben on the details of his funding round, calling him out for using the phrase 'oversubscribed' and rapidly calculating the post-money dilution from the $1.1 million raised at a $5 million valuation.4:03–6:37 · Nathan as informed peer 5/10 Manufacturing Process, Pricing, and Unit Economics Nathan breaks down unit economics on a $36 t-shirt, asking whether 50% gross margin is strong for apparel. Ben explains the proprietary manufacturing advantage of printing before cut-and-sew rather than traditional blank-stamping.6:38–9:10 · Nathan as informed peer 4/10 Organic Marketing, Customer Growth, and User Stories Nathan asks about acquisition metrics and download figures. Ben details his organic content marketing funnel, revealing 3 million total downloads and 100,000 paying customers with high-touch user stories.9:11–11:25 · Nathan as informed peer 5/10 Revenue Metrics and Fall Out Boy Concert Integration Nathan drills into top-line revenue ($3M in 2015, targeting $10M in 2016) and asks how the growth will be achieved. Ben outlines their Fall Out Boy concert integration and SMS marketing funnel.11:26–13:52 · Nathan as informed peer 6/10 Future Vision, Acquisition Valuation, and Retail Disruption Nathan roleplays writing a $10 million buyout check to acquire the company immediately. Ben pushes back on the valuation being too low, laying out a macro case for how retail malls are failing and why Yo Shirt's core tech deserves a much higher multiple.13:52–16:30 · Nathan as informed peer 1/10 Guest Contact Information and Social Handles A brief transition where Ben shares his contact handles before Nathan runs extensive sponsor reads for FreshBooks and HostGator.16:30–19:42 · Nathan as informed peer 4/10 Famous Five: Favorite Business Books on Team Performance Starting the Famous Five, Ben compliments Nathan on his SaaS exit before providing detailed operational insight into how he uses Periscope Data to actively manage vendor backlogs in real time.19:42–21:58 · Nathan as informed peer 3/10 Famous Five: Sleep Routine and Nightly Habits Ben reflects on his sleep tracking data and gives an extended reflection on his 10 years at Apple, detailing the friction between self-taught practical hackers and theoretical Stanford/Berkeley graduates.21:58–22:29 · Nathan as informed peer 1/10 Interview Recap and Final Key Takeaways Nathan provides a rapid-fire recap of Ben's numbers and story before rolling into closing credits and promotional giveaways.0:43–4:02 · Guest teaching 1/10 Top Tribe Weekly Giveaway and Winner Announcement After opening housekeeping and intro, Nathan quickly presses Ben on the details of his funding round, calling him out for using the phrase 'oversubscribed' and rapidly calculating the post-money dilution from the $1.1 million raised at a $5 million valuation.4:03–6:37 · Guest teaching 4/10 Manufacturing Process, Pricing, and Unit Economics Nathan breaks down unit economics on a $36 t-shirt, asking whether 50% gross margin is strong for apparel. Ben explains the proprietary manufacturing advantage of printing before cut-and-sew rather than traditional blank-stamping.6:38–9:10 · Guest teaching 2/10 Organic Marketing, Customer Growth, and User Stories Nathan asks about acquisition metrics and download figures. Ben details his organic content marketing funnel, revealing 3 million total downloads and 100,000 paying customers with high-touch user stories.9:11–11:25 · Guest teaching 2/10 Revenue Metrics and Fall Out Boy Concert Integration Nathan drills into top-line revenue ($3M in 2015, targeting $10M in 2016) and asks how the growth will be achieved. Ben outlines their Fall Out Boy concert integration and SMS marketing funnel.11:26–13:52 · Guest teaching 6/10 Future Vision, Acquisition Valuation, and Retail Disruption Nathan roleplays writing a $10 million buyout check to acquire the company immediately. Ben pushes back on the valuation being too low, laying out a macro case for how retail malls are failing and why Yo Shirt's core tech deserves a much higher multiple.13:52–16:30 · Guest teaching 0/10 Guest Contact Information and Social Handles A brief transition where Ben shares his contact handles before Nathan runs extensive sponsor reads for FreshBooks and HostGator.16:30–19:42 · Guest teaching 4/10 Famous Five: Favorite Business Books on Team Performance Starting the Famous Five, Ben compliments Nathan on his SaaS exit before providing detailed operational insight into how he uses Periscope Data to actively manage vendor backlogs in real time.19:42–21:58 · Guest teaching 5/10 Famous Five: Sleep Routine and Nightly Habits Ben reflects on his sleep tracking data and gives an extended reflection on his 10 years at Apple, detailing the friction between self-taught practical hackers and theoretical Stanford/Berkeley graduates.21:58–22:29 · Guest teaching 0/10 Interview Recap and Final Key Takeaways Nathan provides a rapid-fire recap of Ben's numbers and story before rolling into closing credits and promotional giveaways.0:43–4:02 · Guest disagreement 1/10 Top Tribe Weekly Giveaway and Winner Announcement After opening housekeeping and intro, Nathan quickly presses Ben on the details of his funding round, calling him out for using the phrase 'oversubscribed' and rapidly calculating the post-money dilution from the $1.1 million raised at a $5 million valuation.4:03–6:37 · Guest disagreement 1/10 Manufacturing Process, Pricing, and Unit Economics Nathan breaks down unit economics on a $36 t-shirt, asking whether 50% gross margin is strong for apparel. Ben explains the proprietary manufacturing advantage of printing before cut-and-sew rather than traditional blank-stamping.6:38–9:10 · Guest disagreement 0/10 Organic Marketing, Customer Growth, and User Stories Nathan asks about acquisition metrics and download figures. Ben details his organic content marketing funnel, revealing 3 million total downloads and 100,000 paying customers with high-touch user stories.9:11–11:25 · Guest disagreement 0/10 Revenue Metrics and Fall Out Boy Concert Integration Nathan drills into top-line revenue ($3M in 2015, targeting $10M in 2016) and asks how the growth will be achieved. Ben outlines their Fall Out Boy concert integration and SMS marketing funnel.11:26–13:52 · Guest disagreement 3/10 Future Vision, Acquisition Valuation, and Retail Disruption Nathan roleplays writing a $10 million buyout check to acquire the company immediately. Ben pushes back on the valuation being too low, laying out a macro case for how retail malls are failing and why Yo Shirt's core tech deserves a much higher multiple.13:52–16:30 · Guest disagreement 0/10 Guest Contact Information and Social Handles A brief transition where Ben shares his contact handles before Nathan runs extensive sponsor reads for FreshBooks and HostGator.16:30–19:42 · Guest disagreement 0/10 Famous Five: Favorite Business Books on Team Performance Starting the Famous Five, Ben compliments Nathan on his SaaS exit before providing detailed operational insight into how he uses Periscope Data to actively manage vendor backlogs in real time.19:42–21:58 · Guest disagreement 1/10 Famous Five: Sleep Routine and Nightly Habits Ben reflects on his sleep tracking data and gives an extended reflection on his 10 years at Apple, detailing the friction between self-taught practical hackers and theoretical Stanford/Berkeley graduates.21:58–22:29 · Guest disagreement 0/10 Interview Recap and Final Key Takeaways Nathan provides a rapid-fire recap of Ben's numbers and story before rolling into closing credits and promotional giveaways.0:43–4:02 · Nathan pushing back 4/10 Top Tribe Weekly Giveaway and Winner Announcement After opening housekeeping and intro, Nathan quickly presses Ben on the details of his funding round, calling him out for using the phrase 'oversubscribed' and rapidly calculating the post-money dilution from the $1.1 million raised at a $5 million valuation.4:03–6:37 · Nathan pushing back 2/10 Manufacturing Process, Pricing, and Unit Economics Nathan breaks down unit economics on a $36 t-shirt, asking whether 50% gross margin is strong for apparel. Ben explains the proprietary manufacturing advantage of printing before cut-and-sew rather than traditional blank-stamping.6:38–9:10 · Nathan pushing back 1/10 Organic Marketing, Customer Growth, and User Stories Nathan asks about acquisition metrics and download figures. Ben details his organic content marketing funnel, revealing 3 million total downloads and 100,000 paying customers with high-touch user stories.9:11–11:25 · Nathan pushing back 2/10 Revenue Metrics and Fall Out Boy Concert Integration Nathan drills into top-line revenue ($3M in 2015, targeting $10M in 2016) and asks how the growth will be achieved. Ben outlines their Fall Out Boy concert integration and SMS marketing funnel.11:26–13:52 · Nathan pushing back 5/10 Future Vision, Acquisition Valuation, and Retail Disruption Nathan roleplays writing a $10 million buyout check to acquire the company immediately. Ben pushes back on the valuation being too low, laying out a macro case for how retail malls are failing and why Yo Shirt's core tech deserves a much higher multiple.13:52–16:30 · Nathan pushing back 0/10 Guest Contact Information and Social Handles A brief transition where Ben shares his contact handles before Nathan runs extensive sponsor reads for FreshBooks and HostGator.16:30–19:42 · Nathan pushing back 1/10 Famous Five: Favorite Business Books on Team Performance Starting the Famous Five, Ben compliments Nathan on his SaaS exit before providing detailed operational insight into how he uses Periscope Data to actively manage vendor backlogs in real time.19:42–21:58 · Nathan pushing back 1/10 Famous Five: Sleep Routine and Nightly Habits Ben reflects on his sleep tracking data and gives an extended reflection on his 10 years at Apple, detailing the friction between self-taught practical hackers and theoretical Stanford/Berkeley graduates.21:58–22:29 · Nathan pushing back 0/10 Interview Recap and Final Key Takeaways Nathan provides a rapid-fire recap of Ben's numbers and story before rolling into closing credits and promotional giveaways.

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

0:00 · Nathan 88.7% · guest 11.3%0:00 · Nathan 88.7% · guest 11.3%3:00 · Nathan 38.8% · guest 61.2%3:00 · Nathan 38.8% · guest 61.2%6:00 · Nathan 14.1% · guest 85.9%6:00 · Nathan 14.1% · guest 85.9%9:00 · Nathan 23% · guest 77%9:00 · Nathan 23% · guest 77%12:00 · Nathan 51.7% · guest 48.3%12:00 · Nathan 51.7% · guest 48.3%15:00 · Nathan 72.2% · guest 27.8%15:00 · Nathan 72.2% · guest 27.8%18:00 · Nathan 28.2% · guest 71.8%18:00 · Nathan 28.2% · guest 71.8%21:00 · Nathan 59.3% · guest 40.7%21:00 · Nathan 59.3% · guest 40.7%
Sharpest disagreement ▶ 12:49 Ben rejects hypothetical buyout offer

When Nathan proposes a clean $10 million cash buyout, Ben directly declines the valuation framing, asserting it is far too low given their enterprise technology and audience reach.

 Hardest push from Nathan ▶ 3:06 Nathan challenges oversubscribed framing

Nathan interrogates Ben's choice of words around raising an oversubscribed round, asking if he is trying to create leverage as a 'psychology wizard' before pinning down the exact equity dilution.

 Biggest teaching moment ▶ 13:15 Ben breaks down the macro decline of retail apparel

Ben provides a thorough masterclass on why traditional mall retail is dying among millennials and how mobile-first physical commerce captures social validation in ways legacy brands cannot.

 Nathan holds their own ▶ 3:35 Nathan calculates exact equity dilution on the fly

Nathan instantly parses the priced round mechanics of $1.1 million on a $5 million post-money valuation to calculate that Ben gave up exactly 20% of the company.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Top Tribe Weekly Giveaway and Winner Announcement 6114 After opening housekeeping and intro, Nathan quickly presses Ben on the details of his funding round, calling him out for using the phrase 'oversubscribed' and rapidly calculating the post-money dilution from the $1.1 million raised at a $5 million valuation.
Manufacturing Process, Pricing, and Unit Economics 5412 Nathan breaks down unit economics on a $36 t-shirt, asking whether 50% gross margin is strong for apparel. Ben explains the proprietary manufacturing advantage of printing before cut-and-sew rather than traditional blank-stamping.
Organic Marketing, Customer Growth, and User Stories 4201 Nathan asks about acquisition metrics and download figures. Ben details his organic content marketing funnel, revealing 3 million total downloads and 100,000 paying customers with high-touch user stories.
Revenue Metrics and Fall Out Boy Concert Integration 5202 Nathan drills into top-line revenue ($3M in 2015, targeting $10M in 2016) and asks how the growth will be achieved. Ben outlines their Fall Out Boy concert integration and SMS marketing funnel.
Future Vision, Acquisition Valuation, and Retail Disruption 6635 Nathan roleplays writing a $10 million buyout check to acquire the company immediately. Ben pushes back on the valuation being too low, laying out a macro case for how retail malls are failing and why Yo Shirt's core tech deserves a much higher multiple.
Guest Contact Information and Social Handles 1000 A brief transition where Ben shares his contact handles before Nathan runs extensive sponsor reads for FreshBooks and HostGator.
Famous Five: Favorite Business Books on Team Performance 4401 Starting the Famous Five, Ben compliments Nathan on his SaaS exit before providing detailed operational insight into how he uses Periscope Data to actively manage vendor backlogs in real time.
Famous Five: Sleep Routine and Nightly Habits 3511 Ben reflects on his sleep tracking data and gives an extended reflection on his 10 years at Apple, detailing the friction between self-taught practical hackers and theoretical Stanford/Berkeley graduates.
Interview Recap and Final Key Takeaways 1000 Nathan provides a rapid-fire recap of Ben's numbers and story before rolling into closing credits and promotional giveaways.

Statements from this episode (17)

Disclosure
Williamson: Yo Shirt closed an oversubscribed $1.1M seed round
“So we raised we're oversubscribed around. We ended up closing at 1.1 million. We'd gone up for one.”
Ben Williamson Jun 10, 2016 ▶ 2:59
Assertion Contradicted
Yo Shirt was Kleiner Perkins' first seed-stage investment
“We were the first seed stage investment that they ever made. And we were, you know, very happy to have them in the deal.”
Ben Williamson Jun 10, 2016 ▶ 3:16
Disclosure
Yo Shirt raised its $1.1M round as priced equity
“No, we did a price round.”
Ben Williamson Jun 10, 2016 ▶ 3:33
Disclosure
Yo Shirt raised its seed round at a $5M post-money valuation
“It was five.”
Ben Williamson Jun 10, 2016 ▶ 3:38
Disclosure
Yo Shirt employs 13 full-time staff members
“We've got 13 full-time employees now.”
Ben Williamson Jun 10, 2016 ▶ 4:10
Assertion Not checkable as stated
Yo Shirt ships 95% of custom apparel orders within five days
“And right now, 95% orders ship within five days.”
Ben Williamson Jun 10, 2016 ▶ 4:38
Disclosure
Yo Shirt COGS on $36 t-shirts ranges from $16 to $18
“So cost of goods are between 16 and 18 bucks.”
Ben Williamson Jun 10, 2016 ▶ 5:39
Assertion Not publicly verifiable
Williamson: Apple featured Yo Shirt around 30 times in 2015
“We were featured by Apple several times last year. I think we're like 29 or 30 times we got featured.”
Ben Williamson Jun 10, 2016 ▶ 7:22
Assertion Not publicly verifiable
Williamson: Yo Shirt reached over 3M lifetime downloads
“All in over the life of the app is over three million people that have downloaded the app. There were two million last year.”
Ben Williamson Jun 10, 2016 ▶ 7:26
Assertion Not checkable as stated
Williamson: Yo Shirt has over 100k paying customers
“We have over a 100,000 paying customers.”
Ben Williamson Jun 10, 2016 ▶ 7:40
Assertion Not checkable as stated
Williamson: Yo Shirt generated $3M in top-line revenue in 2015
“So total top line revenue in 2015 was three million dollars.”
Ben Williamson Jun 10, 2016 ▶ 9:19
Disclosure
Williamson: Yo Shirt is targeting $10M in 2016 revenue
“We're shooting for 10.”
Ben Williamson Jun 10, 2016 ▶ 9:25
Assertion Not checkable as stated
Williamson: Yo Shirt boosted Fall Out Boy merchandise sales over 20%
“The Fall Out Boy activation was incredibly successful, and in terms of net overall merchandise, we were able to add over 20% to their merchandise sales.”
Ben Williamson Jun 10, 2016 ▶ 9:57
Opinion
Ben Williamson rejects hypothetical $10M cash buyout offer for Yo Shirt
“I don't know, Nathan. I think that's a little low.”
Ben Williamson Jun 10, 2016 ▶ 12:49
Assertion Not checkable as stated
Williamson: Periscope Data gives Yo Shirt more operational insight than suppliers have
“It's periscopedata.com, and it basically, Nathan, I have better insight into suppliers we work with. I have more insight into their business than they do. And it's because I have real time data.”
Ben Williamson Jun 10, 2016 ▶ 18:30
Opinion
Williamson: Stanford and Berkeley Grads at Apple Couldn't Fix Production Systems
“When I ended up at Apple, I was working with, you know, all these kids coming out of Stanford and Berkeley that had a lot of theory, but couldn't actually do anything. You know, I'd say, hey, you know, we're doing 360 transactions per second to this MySQL data…”
Ben Williamson Jun 10, 2016 ▶ 20:51
Insight
Williamson: Engineers Should Leverage Technical Debt When Testing Uncertain Features
“It's useful to be a hacker and use technical debt for your, you know, as leverage. If you're not sure something's going to work, you've got to be willing to throw it away and you don't want to invest too much.”
Ben Williamson Jun 10, 2016 ▶ 21:28
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