After working for years in early-stage startups and as a journalist, here are three hard truths I’ve learned:
1. Success in Silicon Valley hinges on connections, hard work and luck.
2. Startups often fail because founders lack fundamental business knowledge.
3. Real, actionable advice comes from those who’ve actually done it.
There’s no such thing as “founder DNA.” If you’re willing to take on risk and invest years of your life in something that has maybe a 10% chance of paying off — less if you’re a woman or person of color — you can be a startup founder.
Here’s why I founded Fund/Build/Scale:
1. To help founders make fewer mistakes.
2. To share successful strategies that can accelerate your go-to-market journey.
3. To inspire more people to see themselves as potential founders. There’s a lot of overlooked talent out there, and we are missing out.
This podcast is for anyone who’s interested in learning the basic skills required to launch a startup, secure initial funding and transform an idea into a sustainable business.
I’m talking to guests about everything: finding a co-founder, conducting customer discovery, recruiting early employees, developing a PLG strategy, fundraising when you’re outside a major tech hub — all of it.
Interested? Subscribe to Fund/Build/Scale on all major platforms and follow the podcast on LinkedIn or Substack to get articles, excerpts, transcripts and more.
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After working for years in early-stage startups and as a journalist, here are three hard truths I’ve learned:
1. Success in Silicon Valley hinges on connections, hard work and luck.
2. Startups often fail because founders lack fundamental business knowledge.
3. Real, actionable advice comes from those who’ve actually done it.
There’s no such thing as “founder DNA.” If you’re willing to take on risk and invest years of your life in something that has maybe a 10% chance of paying off — less if you’re a woman or person of color — you can be a startup founder.
Here’s why I founded Fund/Build/Scale:
1. To help founders make fewer mistakes.
2. To share successful strategies that can accelerate your go-to-market journey.
3. To inspire more people to see themselves as potential founders. There’s a lot of overlooked talent out there, and we are missing out.
This podcast is for anyone who’s interested in learning the basic skills required to launch a startup, secure initial funding and transform an idea into a sustainable business.
I’m talking to guests about everything: finding a co-founder, conducting customer discovery, recruiting early employees, developing a PLG strategy, fundraising when you’re outside a major tech hub — all of it.
Interested? Subscribe to Fund/Build/Scale on all major platforms and follow the podcast on LinkedIn or Substack to get articles, excerpts, transcripts and more.
From Engineer to CEO: Ryan Wang on Building Assembled and Finding Product-Market Fit
Fund/Build/Scale
53 minutes
3 weeks ago
From Engineer to CEO: Ryan Wang on Building Assembled and Finding Product-Market Fit
I interviewed Ryan Wang, co-founder and CEO of Assembled, in his San Francisco office to unpack how he turned lessons from Stripe into a fast-growing startup that powers customer support teams at Robinhood, Canva, and Notion.
We talk about:
Finding the right co-founders and surviving a CEO hand-off
Discovering product-market fit by asking one powerful question
Turning a “sleepy” support category into a $200 billion opportunity
Launching a second product with a startup-within-a-startup mindset
What it takes to lead through AI disruption and build for adaptability
Whether you’re building your first team or figuring out your second act, Ryan’s story is a masterclass in scaling deliberately while staying flexible.
RUNTIME 53:40
_
EPISODE BREAKDOWN
(2:35) “ I was employee number 80 or so at Stripe, working on machine learning for fraud detection.”
(5:08) If you’re doing diligent customer discovery, working harder does not get you ahead faster.
(7:27) How Assembled’s founding team, er, assembled.
(8:47) “ There was a period, maybe the first year and a half or so, where there was no CEO.”
(10:33) Ryan explains the mindset that took him from software engineer to CEO.
(12:30) “ ‘Brother mode’ is both a feature and a bug at the same time.”
(14:58) How Assembled arrived at workforce management as its unique value proposition.
(17:48) Ryan talked to more than 100 prospects during the customer discovery process.
(19:00) The exercise they used to develop their initial customer personas.
(22:24) “ We took a really, really long time to hire for product. It was probably four or five years into the company.”
(25:00) Who was Assembled’s first design hire?
(27:26) To acquire product-market fit, “ we started with just a simple automation value proposition.”
(30:26) “ A lot of folks wanted to invest in Stripe alums, and Stripe led our seed.”
(33:35) Why customer support ops is — and will continue to be — such a huge opportunity.
(36:41) A good mission statement defines the change you want to see in the world.
(41:41) “ People who really do feel committed to a large mission, they understand that to get there is gonna require a lot of schlep.”
(43:55) How Assembled used a startup-within-a-startup mindset to innovate.
(48:47) “ We reassigned folks internally, and the key really was the order of operations.”
(51:31) If you were interviewing for a job with an early-stage startup, what’s one question the CEO would have to answer before you could take the offer?
LINKS
Assembled
Ryan Wang
Brian Sze
John Wang
Stripe
Kelly Sims, Thrive Capital
Jack Altman, Alt Capital
Jen Ong Vaughan, Head of Strategic Ops, Stripe
SUBSCRIBE
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Thanks for listening!
– Walter.
Fund/Build/Scale
After working for years in early-stage startups and as a journalist, here are three hard truths I’ve learned:
1. Success in Silicon Valley hinges on connections, hard work and luck.
2. Startups often fail because founders lack fundamental business knowledge.
3. Real, actionable advice comes from those who’ve actually done it.
There’s no such thing as “founder DNA.” If you’re willing to take on risk and invest years of your life in something that has maybe a 10% chance of paying off — less if you’re a woman or person of color — you can be a startup founder.
Here’s why I founded Fund/Build/Scale:
1. To help founders make fewer mistakes.
2. To share successful strategies that can accelerate your go-to-market journey.
3. To inspire more people to see themselves as potential founders. There’s a lot of overlooked talent out there, and we are missing out.
This podcast is for anyone who’s interested in learning the basic skills required to launch a startup, secure initial funding and transform an idea into a sustainable business.
I’m talking to guests about everything: finding a co-founder, conducting customer discovery, recruiting early employees, developing a PLG strategy, fundraising when you’re outside a major tech hub — all of it.
Interested? Subscribe to Fund/Build/Scale on all major platforms and follow the podcast on LinkedIn or Substack to get articles, excerpts, transcripts and more.
