Fund/Build/Scale

If you work in tech long enough, there’s a good chance you’ll go through a layoff. Either your own, or one that leaves you wondering whether you’re next.

Shanon Olsen, COO of Henley Leadership, works with executives and organizations navigating growth, disruption, and change. In this episode, we talk about why layoffs should be understood as a cultural breakdown rather than a one-day event, what happens when founders build companies they aren’t prepared to lead, and why CEOs can delegate just about everything — except culture.

I’ve been on both sides of this equation, so I asked Shanon about how to stay committed to your work without making your employer your identity, why it’s important to maintain relationships outside your company, how to assess whether a workplace is recovering after layoffs, and why staying in a job and exploring other possibilities don’t have to be mutually exclusive.

RUNTIME 48:52
 

EPISODE BREAKDOWN
(2:05) When does a startup stop being a startup? 

(9:37) If you're not ready to let someone go, you shouldn't be the CEO

(14:57) Why layoffs are a "cultural breakdown" 

(19:56) How should the CEO behave after layoffs? 

(23:50) Building a culture that's resilient enough to weather layoffs

(26:58) How to tell an employee WHY you're laying them off

(32:38) " Identify what's your purpose outside of your position." 

(39:13) How to tell if your company is recovering after layoffs 

(44:23) Should you stay or leave after layoffs?

 

📺 Watch this episode on YouTube: https://youtu.be/vbunRx4FZIQ

 

LINKS

Shanon Olsen

Henley Leadership Group

Navigating Layoffs: Understanding the Impact on You and Your Team, Henley Leadership Group

Who Do We Choose To Be, Margaret Wheatley

Dunbar’s Number

Johari Window

Are you building something that’s hard to explain?
That’s often a sign you’re working on something interesting, but it raises the risk that you’re missing out on fundraising, sales, hiring, and media opportunities.

I help early-stage founders sharpen the narrative: what matters, why now, who needs to care, and why they’re the right team to make it happen.

If you’re preparing for a raise, launch, important customer meeting, panel, or hiring push, I can help you pressure-test the story before the stakes get higher.

Visit the Fund/Build/Scale website to learn more, or email fundbuildscale@gmaii.com

👉🏾 Learn more

 

📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/

 

 

📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw

America is getting older. Tens of millions of people are caring for parents, grandparents and other family members. The problems are everywhere, and many of them are painful, expensive and still poorly served by technology.

That does not mean every care-related startup is a good business, however.

Tatyana Zlotsky, CEO of A Place for Mom, joins me to talk about what founders need to understand before building for older adults and the people who care for them.

We discuss why "seniors" aren't a single customer segment, how to conduct customer research in a market you don't know, and why founders need to distinguish between the person using a product, the person making the decision and the person actually paying for it. 

Tatyana also explains why private-pay and insurance-backed businesses require fundamentally different approaches, and shares the story of a founder who spent more than a year changing course after discovering he'd chosen the wrong customer.

We also dig into AI. Tatyana explains why starting with what the technology can do is backwards, why proprietary customer data can create a meaningful advantage, and why founders should ask whether they're really building something that general-purpose AI can't already provide.

This is a conversation about finding real problems, understanding who you're solving them for, and building businesses around customer needs instead of technology trends.

RUNTIME 38:51
 

EPISODE BREAKDOWN
(2:21) Tatyana Zlotsky’s path to A Place for Mom

(4:46) Why senior care remains an underbuilt market

(9:20) The real problems caregivers need solved

(12:36) Why “seniors” aren’t a single customer segment

(16:31) How to do customer research in the care market

(20:35) Why “AI for X” isn’t a business strategy

(24:02) Private pay vs. insurance: deciding who pays

(26:50) What happens when founders choose the wrong business model

(28:59) The senior-care product Tatyana wishes someone would build

(33:24) What makes a care startup worth taking seriously

(36:19) Why families shouldn’t wait for a care crisis

LINKS
Tatyana Zlotsky

A Place For Mom

Oura

Fitbit

Are you building something that’s hard to explain?
That’s often a sign you’re working on something interesting, but it raises the risk that you’re missing out on fundraising, sales, hiring, and media opportunities.

I help early-stage founders sharpen the narrative: what matters, why now, who needs to care, and why they’re the right team to make it happen.

If you’re preparing for a raise, launch, important customer meeting, panel, or hiring push, I can help you pressure-test the story before the stakes get higher.

Visit the Fund/Build/Scale website to learn more, or email fundbuildscale@gmaii.com

👉🏾 Learn more

SUBSCRIBE
📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/

 

📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw

 

📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/

If you have a startup idea, how do you know whether you’re onto something—or just really good at convincing yourself?

Pete Martin has spent his career finding out. He’s worked at six cybersecurity startups, most of them in the pre-product, pre-revenue days, with two IPOs along the way. Today, he’s CEO and co-founder of Realm Security.

In this episode, we get tactical about finding the right early adopters, running customer discovery that produces actual signal, recognizing patterns in the feedback, and knowing when someone’s interest is strong enough to ask a question that makes a lot of founders uncomfortable: 

Would you pay for this?

And if you’ve got an idea but aren’t ready to quit your day job, Pete lays out a seven-day experiment you can run to start finding out whether there’s really something there.

RUNTIME 36:19
 

EPISODE BREAKDOWN
(1:51) What does Realm do today, and who's buying it?

(3:28) Finding the right early adopters

(8:01) Where to locate your first potential customers

(12:54) Why customer discovery requires volume

(18:55) How to write outreach that gets a (positive) response

(21:05) When to say no to a potential customer

(23:48) Sell the outcome, not the features

(28:33) A seven-day experiment to test your startup idea

(33:01) When is it time to hire a sales team? 

LINKS
Pete Martin

Realm Security

Are you building something that’s hard to explain?
That’s often a sign you’re working on something interesting, but it raises the risk that you’re missing out on fundraising, sales, hiring, and media opportunities.

I help early-stage founders sharpen the narrative: what matters, why now, who needs to care, and why they’re the right team to make it happen.

If you’re preparing for a raise, launch, important customer meeting, panel, or hiring push, I can help you pressure-test the story before the stakes get higher.

Visit the Fund/Build/Scale website to learn more, or email fundbuildscale@gmaii.com

👉🏾 Learn more

SUBSCRIBE
📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/

 

📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw

 

📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/

Peter Wang is co-founder and Chief AI and Innovation Officer at Anaconda, a company he helped start in 2012 after years of working as a software developer and consultant.

In this episode, Peter draws on Anaconda’s early days and the entrepreneurship lessons he shares with scientists and engineers at Cornell to explain what technical people need to learn when they launch a company.

We talk about learning to ask better questions instead of rushing to provide answers, recognizing the limits of what you know, and treating yourself as an investor when deciding whether an idea is worth pursuing.

Peter also explains his approach to customer discovery, why employees are investors too, and how aspiring founders can practice entrepreneurship by building something — however small — that someone will actually pay for.

 

RUNTIME 43:00
EPISODE BREAKDOWN
(1:53) Finding the Product by Doing the Work

(10:19) "I'm just sharing my own field notes on what I had to learn."

(14:05) Know the Limits of What You Know

(18:18) Climbing the Ladder of Disbelief 

(23:59) Customer Discovery: Listen, Validate, Explore

(29:02) "Your employees are also investors."

(31:02) " It's really incredibly important that the vision is compelling for people."

(38:39) An Exercise for Entrepreneurship

 

📺 Watch this episode on YouTube: https://youtu.be/GuysuVrGd8Y

LINKS
Peter Wang

Anaconda

Swim With the Sharks Without Being Eaten Alive,  Harvey Mackay

Are you building something that’s hard to explain?
That’s often a sign you’re working on something interesting, but it raises the risk that you’re missing out on fundraising, sales, hiring, and media opportunities.

I help early-stage founders sharpen the narrative: what matters, why now, who needs to care, and why they’re the right team to make it happen.

If you’re preparing for a raise, launch, important customer meeting, panel, or hiring push, I can help you pressure-test the story before the stakes get higher.

Visit the Fund/Build/Scale website to learn more, or email fundbuildscale@gmaii.com

👉🏾 Learn more

SUBSCRIBE
📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/

 

📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw

Canvas Prime Co-founder and Managing Director Rebecca Lynn has spent 25 years in venture capital, backing companies including LendingClub, Doximity and Casetext and helping founders navigate more than a dozen exits.

In this conversation, we get into why taking venture capital puts founders on a path toward liquidity, and why an IPO isn't the only outcome worth building toward.

Rebecca explains how founders can develop relationships with potential acquirers years before they're ready to sell, when it makes sense to bring in a banker or strategic advisor, and how Casetext built the relationships that eventually led to its acquisition by Thomson Reuters.

We also talk about why founders should get an offer on paper before trying to improve it, how to negotiate without overplaying your hand, what to watch for with earnouts and other deal terms, and how to make sure employees aren't forgotten when a company gets sold.

 

📺 Watch on YouTube: https://youtu.be/5kV4SvM9rBY

RUNTIME 40:51
 

EPISODE BREAKDOWN
(2:17) Creating Strategic Options

(8:50) What Taking Venture Capital Really Means

(11:42) Don't Build to Sell; Build Strategically 

(15:18) How Casetext Built Toward an Exit  

(21:39) Where Acquisition Offers Come From 

(27:54) "If it's not on paper, it's not real."

(33:02) Price Isn't the Only Thing That Matters

(35:22) Take Care of Your Employees

(37:32) How to Get M&A Ready

LINKS
Rebecca Lynn, LinkedIn

Canvas Prime

Thomson Reuters Completes Acquisition of Casetext, Inc.

Doximity

Lending Club

Gabi

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Are you building something that’s hard to explain?

That’s often a sign you’re working on something interesting, but it raises the risk that you’re missing out on fundraising, sales, hiring, and media opportunities.

I help early-stage founders sharpen the narrative: what matters, why now, who needs to care, and why they’re the right team to make it happen.

If you’re preparing for a raise, launch, important customer meeting, panel, or hiring push, I can help you pressure-test the story before the stakes get higher.

Visit the Fund/Build/Scale website to learn more, or email fundbuildscale@gmaii.com

👉🏾 Learn more

SUBSCRIBE
📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/