In most industries, if you’ve got a solid idea, a few engineers, and a working prototype, you can at least get in the game.

Professional sports is not one of those industries.

When Jordy Leiser co-founded Jump with Alex Rodriguez and Marc Lore, he wasn’t just building software — he was trying to rebuild the entire fan experience from the ground up, in a business dominated by legacy players like Ticketmaster. 

Four years later, his company is powering the digital backbone for teams like the Minnesota Timberwolves and North Carolina Courage.

In this episode, Jordy explains what it actually takes to break into a closed industry, why he reverse-engineers every funding round before he raises it, and the biggest mistake he refused to repeat as a second-time founder.

(1:12) Breaking into pro sports, rebuilding fan experience, and reverse-engineering fundraising.

(2:03) How Stella Connect (customer service) laid the foundation for Jump (customer experience for fans).

(5:46) Why sports is nothing like building a typical SaaS startup — more like a “car company” level of complexity.

(9:54) Early customers as classic early adopters — every team already knows the pain points intimately.

(11:25) The first hypothesis they had to kill: incumbents don’t want to integrate or share data. At all.

(15:06) Sports as an industry you can’t “hack into” — it works more like fashion or Hollywood.

(19:45) Jump’s origin as a “dynamic seating” idea — and why they had to build the entire platform instead.

(27:01) Seed to Series A timeline — and how the Timberwolves sale collapsing delayed everything by a year.

(34:39) What he had to unlearn from Stella Connect: stop zooming in — zoom way out to a 10–20-year vision.

(45:40) Hiring from big tech: what’s actually transferable, and the dangers of logo-blindness.

Jordy Leiser

Jump

Alex Rodriguez

Marc Lore

Jump Series A announcement

Delivering Happiness: A Path to Profits, Passion, and Purpose, Tony Shieh

Effectuation — UVA Darden School of Business

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Thanks for listening!

 – Walter

Most founders think VCs want a pitch deck full of market numbers, a roadmap, and a feel-good story about the future.

Hoxton Ventures Partner Payton Dobbs isn’t looking for any of that.

He wants to know if you actually understand the game you’re trying to play.

In this conversation, Payton breaks down the tactical stuff founders almost always get wrong:

He also talks about category creation, how to hire in the U.S. if you’re coming from Europe, why pricing is a strategic weapon, and the number-one question he asks every founder — the one that quietly decides whether you’re playing at venture scale or not.

If you’re an early-stage builder, this episode will help you level up before you start meeting with VCs.

02:12: Payton Dobbs’ background and the value of building presence in key markets

03:25: Not all good ideas are venture scale: how to assess billion-dollar potential

04:01: Why new category creation is crucial for venture scale startups

06:35: What VCs look for in a pitch deck: TAM, SAM, and logic behind the numbers

08:06: Case study: Deliveroo and building new markets from small segments

09:07: Identifying pain points and leveraging founder expertise

10:57: Advice for technical founders: the value of complementary co-founders and commercial skills

12:23: Building frameworks: due diligence on markets, competitors, and learning from others’ mistakes

13:54: Adapting go-to-market strategies for different business models (B2B SaaS, consumer, etc.)

15:00: The importance of having a perspective and being able to debate your point of view

15:50: Solo founders vs. teams: most are teams, but solo founders can succeed too

13:28: The state of the AI ecosystem in Europe and why it’s accelerating

17:18: Navigating US immigration and talent: why keeping dev teams in Europe can be strategic

20:34: Common mistakes when entering the US: “If you build it, they will not come”

21:21: Do you need to reboot customer discovery in new markets? Sometimes, but not always

22:24: The importance of understanding the competitive landscape and customer needs in each market

24:54: Hiring in the US: cultural differences and what to look for in team members

27:33: Payton’s parting advice for founders expanding to the US: grind, network, and be relentless

28:36: Building sales ops from scratch: tools, systems, and process before people

32:05: Understanding and accruing value in the business value chain

34:45: Signals that a team can move from tech to traction: agility, speed, and adaptability

36:37: Pricing as an art and a science; lessons from Nest and Apple

40:00: Metrics: NPS, customer surveys, and forward-looking indicators

44:42: What Payton hopes to unlock for founders by being based in the US

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Thanks for listening!

– Walter.

Today’s episode is something a little different. 

I’m doing a feed swap with Humans of AI, a podcast from the team at Writer. 

What you’re about to hear is their conversation with David Ryan Polgar, the Founder and President of All Tech Is Human, a leading organization in the Responsible Tech movement.

He’s a pioneer in tech ethics and responsible innovation, and someone who’s been thinking about the societal impact of AI long before it was mainstream.

If you’re building in AI, investing in it, or just trying to understand where this whole industry is headed, his perspective is a valuable counterweight to the hype cycles.

************

On this episode of Humans of AI, presented by Writer, we’re joined by David Polgar, founder of All Tech is Human, a non-profit and community dedicated to bringing together people, organizations, and ideas to grow and strengthen the Responsible Tech ecosystem. David shares some harrowing stories from the early days of social media that led him to where he is today – at the intersection of tech and human rights, AI and ethics. A lawyer and educator at the forefront of a movement “altering the DNA of tech development,” David is determined to create spaces and communities for human conversations and connections so that together we can shape the future of AI. 

Subscribe now so you don't miss an episode! 

Check out Writer’s Youtube channel to watch the full interviews. 

Learn more about Writer at writer.com. 

David Ryan Polgar

Humans of AI: Presented by Writer (podcast)

Navigating the ethical implications of generative AI with All Tech Is Human’s David Polgar (Writer blog)

Alaura Weaver

Communicating Your Vision with May Habib (CEO, Writer) and Gaurav Misra (CEO, Captions)

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Thanks for listening!

– Walter.

Recorded live in San Francisco during TechCrunch Disrupt 2025 week, this Fund/Build/Scale session brings together Cyan Banister (Long Journey Ventures) and Cristian Cibils Bernardes (Autograph) for a practical look at building consumer AI and the investor-founder dynamics that make it work. We dig into pre-traction signals that actually predict momentum, how to validate a weird idea, raise smart money, and ship products people return to. Cristian shares Autograph’s first moment of value, retention indicators, and a trust-by-design stance; Cyan unpacks the decision rules and behaviors that earn a second meeting. Together, they outline small-budget experiments and the frameworks they use to create products that stick. For first-time founders and early operators, this episode delivers concrete steps you can start taking tomorrow.

Thanks very much to Jenna Birch and the team at SISU for co-hosting and making this live recording possible!

(1:54) Why Cristian named Autograph’s AI agent “Walter.”

(3:37) When they connected, Cristian saw “a bunch of synchronicities along the way that just kept pointing in this direction.”

(4:59) Cyan: “When he showed up and we were sitting together having coffee, I immediately was like, ‘yes.’”

(6:03) The sheer number of coincidences linking these two is unsettling — “quantum entanglement” comes to mind.

(8:18) Cristian and Cyan share their non-consensus takes on consumer AI.

(10:53) Cyan describes the framework she’s using to assess early signals as an investor.

(12:51) “I will not look at your résumé. I won’t look at what you did. Whatever you tell me in that interview is what I’m going to go off of.”

(14:42) “Fundraising is grueling. It was 50 conversations before I met Cyan, and then I had, I think, another 30.”

(16:53) Cyan’s framework for backing vs. passing.

(18:26) The three essential ingredients Long Journey Ventures seeks in founders.

(22:00) What a “magically weird” founder looks like — and why they’re so valuable.

(26:15) A red flag that ensures you won’t get a second meeting with Cyan.

(27:52) A behavior that virtually guarantees a second meeting.

(29:45) Cristian describes Autograph’s moat.

(34:40) “This whole thing doesn’t work if the trust element isn’t there.”

(38:08) What founder-investor fit looks like in their working relationship.

(41:57) One experiment founders should run this week.

(43:10) The most underrated founder superpower.

(44:10) “If you were interviewing for a job at an early-stage startup, what’s one question you’d have to ask the CEO before you could take the offer?”

📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/

Thanks for listening!

– Walter.

***********************************

This event and recording are independently produced by Fund/Build/Scale and co-hosted with SISU. We are not affiliated with, endorsed by, or sponsored by TechCrunch or TechCrunch Disrupt. “TechCrunch” and “Disrupt” are trademarks of their respective owners.

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:

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.

_

(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?

Assembled

Ryan Wang

Brian Sze

John Wang

Stripe

Kelly Sims, Thrive Capital

Jack Altman, Alt Capital

Jen Ong Vaughan, Head of Strategic Ops, Stripe

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Thanks for listening!

– Walter.

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.

(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. 

Chris Barbin

Tercera

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Thanks for listening!

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.

(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? 

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Thanks for listening!

– Walter.

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:

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.

(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.

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Thanks for listening!

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.

(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.

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Thanks for listening!

Frontier tech startups don’t fail because the science is bad — they fail because no one needs what they’re building.

In this episode, Roadrunner Venture Studios CEO/co-founder Adam Hammer explains how to avoid that fate. 

We talk about why the U.S. struggles to turn research into startups, why being right isn’t enough, and what it really takes to cross the Valley of Death between lab science and real-world demand.

Along the way, Adam shares practical insights for first-time founders, including:

If you’re building something deep, hard, or new — don’t skip this one.

(2:32) How a career spanning national labs, venture capital, and startup leadership led to Roadrunner Venture Studios.

(7:46) “ Our goal is to compress all the mistakes that you would make in a three-year period into a year.”

(8:50) The three frontier tech sectors Roadrunner focuses on: advanced energy, advanced manufacturing, and advanced compute.

(10:28) Why it’s so hard to translate lab science into sustainable, venture-scale businesses.

(13:49) Adam shares ideas for bridging America’s structural gap in commercializing frontier tech.

(16:38) “ Roadrunner serves as a de-risking mechanism for ideas and for people.”

(21:12) “ In science, you win by being right. But in startups, you win by being useful.”

(24:23) What Adam looks for in a pitch deck.

(27:15) When it comes to sourcing founders and ideas, “ we are as early as it gets.”

(31:54) Why Roadrunner Venture Studios set up shop in New Mexico.

(34:16) If he could fix one common founder misconception, what would it be?

(36:26) “ There's nothing innate that predetermines whether somebody can or cannot be a founder.”

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Thanks for listening!

– Walter.