Fund/Build/Scale

• 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   📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!   – Walter.  

  --------  

  53:40

  --------

  53:40
• The Starting Five: How to Build a Leadership Team That Can Scale

  When startups fail to scale, it’s rarely because of bad code or bad luck. More likely, it's because they didn’t hire the right people at the right time. Chris Barbin, founder and CEO of Tercera, shares a playbook for assembling your “Starting Five” — the essential leadership roles every professional services startup needs to grow from $10M to $100M and beyond. Drawing from decades as an operator and investor, he explains how to spot founder-market fit, when to swap out co-founders, and why hiring someone with a flashy resume can set you back two years. If you’re building a people-first business, this episode is your blueprint for doing it right the first time. RUNTIME 35:14   EPISODE BREAKDOWN (2:24) Chris explains how his career path led him to become CEO of Tercera. (6:18) The most common problems and challenges he helps founders navigate. (9:17) What stage are the professional services startups Chris typically meets with? (11:06) How he defines founder-market fit. (13:31) Red flags that indicate a founder isn’t ready to work with investors. (16:15) One of the constructs of our fund is [that] none of our investments compete with each other.” (17:34) After the CEO, “ those five supporting cast members — key lieutenants — are essential.” (19:11) In most cases, three of the original Starting Five need to be replaced. (22:29) “ I've fallen into that trap myself — I hired a bunch of those that look amazing on paper.” (24:29) A framework for finding your first executive marketing hire. (27:17) Don’t let your board pressure you into making rushed staffing decisions. (29:37) Managing the ripple effects associated with rebuilding the Starting Five “is really, really hard to do.” (31:29) Chris shares his preferred format for board meetings. (33:00) The one thing he wishes every founder understood before they started raising money.  LINKS Chris Barbin Tercera SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ Thanks for listening!  

  --------  

  35:14

  --------

  35:14
• From Code to Customer: The Strategic Power of a Field CTO

  I’ve explored different aspects of product-market fit on the podcast, but when you’re scaling an open-source business with enterprise customers and a global developer community, you also need customer–engineering fit — the ability to translate between what’s being built and what the market actually needs. At Astronomer, Viraj Parekh is that bridge. He is part engineer, part strategist, and part customer advocate, working across product, sales, and engineering. In this episode of Fund/Build/Scale, Viraj explains what a Field CTO really does, how the role evolved at Astronomer, and when founders should consider creating one. He also shares lessons on customer discovery, team dynamics, and how to turn technical insight into business momentum. RUNTIME 31:16 EPISODE BREAKDOWN (2:20) What is Astronomer, and when did the company get started? (3:51) How the founding team came together. (6:39) How Viraj collaborated with CTO Julian LaNeve to develop the Field CTO role. (8:28) Where their roles overlap — and where they each take ownership. (11:42) “We were at a point where we were really trying to standardize our sales process.” (13:20) How the Field CTO role is different from a sales engineer or solutions architect. (15:39) “ Talking to customers is a very humbling thing every day because you just realize how much you have to learn.” (19:14) “ At a really early stage of customer development, the Field CTO role is almost like an external-facing product manager.” (21:46) Viraj talks about the processes and tools he uses to share customer feedback internally. (24:48) How to be a staunch customer advocate without losing your business focus. (26:55) What’s the biggest opportunity cost associated with not having a Field CTO? (30:13)  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 Viraj Parekh Julian LaNeve Astronomer Apache Airflow SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

  --------  

  31:16

  --------

  31:16
• Dead Weight on the Cap Table: Inside the Ugly World of Founder Breakups

  More startups die from co-founder breakups than from running out of money. Attorney David Siegel, a partner at Grellas Shah LLP, has spent years inside these conflicts, helping founders navigate everything from equity disputes to emotional meltdowns. In this conversation, he explains: Why greed and mismatched expectations trigger so many founder breakups How minority founders can protect themselves before they’re pushed out What departing founders can realistically expect to walk away with Why VCs hate “dead weight” on the cap table The emotional toll of disputes — and why lawyers often play part therapist If you’re thinking about starting a company with someone else, or already rowing in that two-person boat, this episode will show you what’s at stake — and what to do before it’s too late. If you thought The Social Network had a happy ending, you might want to skip this one. RUNTIME 47:35 EPISODE BREAKDOWN (2:15) Disclaimer: “If you're looking for legal advice, that's something to talk to your own lawyer about.” (4:14) When it comes to equity distribution, “the fifty-fifties are a 5%.” (7:14) What are the most common triggers that lead to co-founder breakups? (11:35) What steps can a minority co-founder take to protect their equity in the earliest stages? (15:23) Ultimately, “the only person the lead investor knows is the majority founder.” (17:06) As long as you document all oral agreements, “you should be in good shape.” (20:04) Draw up agreements for any advisors or consultants you add to the cap table. (22:36) “The initial calls around a co-founder dispute, we play 50% lawyer, 50% therapist.” (25:17) “Breakups where it's not a surprise to the founder being kicked out are usually the smoothest.” (28:05) Once outside money comes in, minority co-founders leave with less than they agreed to. (30:09) How negotiable is retaining the co-founder title after a breakup? (32:32) Pre-agreed severance and other ideas for reducing financial pain and hard feelings. (35:05) “What a minority founder can do: you need face time with the investor.” (38:44) When should the founder with less equity contact a lawyer? (41:15) The most common mistakes founders make during a breakup. (44:43) The one thing David wishes more founders understood before picking a co-founder or investor. LINKS David Siegel Grellas Shah LLP SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

  --------  

  47:35

  --------

  47:35
• An Operator’s Playbook for Monetizing Product-Led Growth

  What do you do when everyone loves your product but no one’s paying for it? That was the challenge facing Beautiful.ai. Founder Mitch Grasso nailed the product, but to build a sustainable business, he brought in operator Jason Lapp as CEO. In this conversation, Jason shares how Beautiful.ai killed its freemium tier, introduced a credit-card-gated trial without losing momentum, and learned to serve both self-serve and enterprise customers at the same time. He also explains how to listen to customer feedback without becoming a feature factory, and why non-technical founders shouldn’t try to know everything about the tech stack. If you’re a founder wondering when to put up a paywall — or how to balance PLG with enterprise sales — here's a playbook. RUNTIME 46:20 EPISODE BREAKDOWN (3:35) “ The timing of us coming together was really fortuitous for beautiful because he had already built the first version of beautiful and put it in market.” (6:28) “ Microsoft and Google report that there's close to a billion people that use presentation software on a monthly basis.” (10:51) “ At a certain point after getting in market, you start to get a different set of signal.” (14:52) The free trial period is a great opportunity to learn about what customers value most. (19:56) Leverage “emotional” feedback to improve the customer experience. (23:46) “ We do have a guiding principle, which is: on the customer side, we generally don't build for one customer need.” (26:17) Beautiful.ai uses NPS surveys to gather feedback from enterprise and individual users. (28:49) Since pivoting to paid, they have separate teams for enterprise and individual customers. (23:02) “ We think about an ICP, and then we think about an IECP, meaning the enterprise as a whole.” (33:57) Capturing behavioral and attitudinal data to understand customer behavior. (37:18)  How the broader rise of generative AI has influenced GTM strategy. (42:33) Jason shares some advice for non-technical CEOs. LINKS Jason Lapp Beautiful.ai AI Isn’t Coming For Jobs, It’s Coming For Inefficiency Continuous Discovery Habits: Discover Products that Create Customer Value and Business Value, Teresa Torres Everything You Need to Know About Freemium Pricing, Kyle Poyar, OpenView Partners SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

  --------  

  46:20

  --------

  46:20

Mais podcasts de Notícias

Podcasts em tendência em Notícias

Sobre Fund/Build/Scale

Fund/Build/Scale: Podcast do grupo