Fund/Build/Scale

How to run a board meeting in 60 minutes

If you want a healthy relationship, it’s essential to set clear expectations and boundaries from the start. 
The same holds true for a founder and their board. Despite the power dynamics, CEOs can still create a transparent communication framework that respects everyone’s limited time.
In part two of my interview with TigerEye co-founder and CEO Tracy Young, we discuss her approach to work-life balance, the unique challenges women founders face while fundraising, how to run a board meeting in 60 minutes, and the importance of gaming out worst-case scenarios.
Runtime: 24:58
EPISODE BREAKDOWN
(2:20) Why traditional 80-page board decks are “just not helpful for strategic discussion.”
(5:32) How Tracy structures memos for board meetings.
(7:18) The importance of gaming out worst-case scenarios with your team.
(9:31) “Our motto is: ‘go towards where it hurts.’ Go fix it.”
(12:40) Tracy and (co-founder/husband) Ralph’s approach to work-life balance.
(15:26) “It's trite to say, but I try to meditate when I can.”
(17:11) “I have met a lot of women founders who have told me horrific
stories.”
(20:24) “You look at who's writing the checks and are actually decision makers. They lean more towards male — actually white males.”
(22:59) “You shouldn't be talking to customers in one meeting and in the same day meeting investors.”
(23:48) The one question she’d have to ask a CEO if she were interviewing for a startup job.
LINKS
Tracy YoungWhy I started TigerEye
Early-stage board decks are dead: How to run a meeting in 60 minutes
TigerEye
Ralph Gootee
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📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/
📓Substack: https://fundbuildscale.substack.com
Thanks for listening!
-- Walter.
 

Starting up in stealth: A conversation with TigerEye co-founder/CEO Tracy Young

In 2011, Tracy Young co-founded PlanGrid, which made software for construction teams. After scaling the company to 450 people and raising $69 million, it was acquired by Autodesk in 2018 for $875 million.
That’s a win, but Tracy and her partners didn’t go for the exit because they’d reached the peak of the mountain.
They cut the deal because PlanGrid was behind in the market, and they didn’t know how to catch up.
Three years later, during the pandemic, Tracy and her husband, Ralph Gootee, co-founded TigerEye, a RevOps AI agent that lets analysts answer questions and allocate resources based on data that’s updated multiple times each hour. 
Last year, TigerEye closed a $30 million Series A.
She describes it as “moneyball for business,” the tool she wished she’d had at PlanGrid when she was fighting entrenched competitors who were just better at enterprise sales. 
In part one of our interview, she explains why they started their new company up in stealth and how TigerEye reflects her vision of what enterprise software should accomplish.
She also shared what she’d learned as a CEO her second time around about building early teams and managing a hybrid workplace.
Subscribe now to get part 2:
Her approach to work-life balance
The unique challenges women founders face while fundraising
How to run a board meeting in 60 minutes, and
The importance of gaming out worst-case scenarios.
Runtime: 23:09
EPISODE BREAKDOWN
(2:53) TigerEye’s origin story: “We wanted a second chance, and that became a big desire of ours.”
(5:11) “There's certain decisions that only leadership and the CEO can make.”
(7:58) “We just really sucked at selling to the enterprise.”
(9:53) How to manage customer discovery while you're in stealth.
(15:53) Tracy’s tactics for managing a remote-first team effectively.
(19:25) When it comes to personnel, it’s “much harder to be mediocre at a small startup.”
(21:21) Why she still interviews every new hire at TigerEye.
LINKS
Tracy Young
Why I started TigerEye
5 failure points between 5 and 100M ARR 
TigerEye
Ralph Gootee
SUBSCRIBE
📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/
📓Substack: https://fundbuildscale.substack.com
Thanks for listening,
-- Walter.

“Talent has no ZIP code:” Laura González-Estéfani on building startups outside Silicon Valley

Most of the world’s talent goes untapped. Unrecognized.
With that in mind, I interviewed Laura González-Estéfani, founder of Miami-based VC firm TheVentureCity in May 2024.
We talked about the potential of global talent and why more investors need to broaden their scope beyond major tech hubs.
This episode provides valuable insights for founders who don’t have large networks or a business background. She offered practical advice on navigating the VC approval process, building trust with investors, and avoiding common pitfalls such as overdilution of equity.
She also talked about what she’s looking for, and how she prefers to be pitched.
Runtime: 45:01
LINKS
Laura González-Estéfani
TheVentureCity
Growth Scanner
AHA (beta)
TheVentureCity jobs board
SUBSCRIBE
📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/
📓Substack: https://fundbuildscale.substack.com

“Cultural fit” is a polite way to say “personal bias”

Today is my 55th birthday!
I was planning to take the day off, but I started thinking about a few people my age who work in tech and have been recently laid off.
Unlike workers in their 20s and 30s, they’re facing a very different set of pressures: family, college payments, aging parents, retirement, etc. Most of the ones I know are having a hard time landing interviews, let alone full-time jobs.
This is the shortest episode I’ve ever released, so technically, I guess that makes this a hot take. I generally avoid those, but it’s my birthday and I’m feeling self-indulgent. 🎂🥳
Thanks for listening!
Runtime: 5:05
LINKS
Michael Tritter
Carlos Chairez
UCSF Trigeminal Neuralgia Clinic
Subscribe to Fund/Build/Scale
📥LinkedIn
📓Substack 
Thanks for listening!
– Walter.

Shaping the future of work and care: Courtney Leimkuhler + Elana Berkowitz of Springbank

Based in New York, Elana Berkowitz and Courtney Leimkuhler are co-founders and partners at Springbank, where they focus on sectors that support working women and their families, largely in three key areas: the future of work, the care economy, and household consumer services. 
Their thesis is driven by growing demand from employers, insurers, and the government, recognizing the economic impact of caregiving, which includes fields like teaching, child care, nursing and home health care.
“We look at the infrastructure to serve the needs of working women and their families as something that's underfunded, under-innovated, and kind of a huge opportunity hiding in plain sight,” said Elana.
We talked about backing solutions that combine business acumen with empathy for care workers while considering ethical AI use. They also shared insights on how to pitch effectively, stressing the importance of addressing the 'how' alongside the opportunity size.
Runtime: 39:53
EPISODE BREAKDOWN
(1:21) Courtney and Alana share Springbank VC’s origin story.
(4:03) Their investment thesis: the care economy, future of work, household services.
(7:01) Why their investment in Carefull “is really levered to this concept of financial caregiving.”
(11:23) How they recognize founder-market fit.
(15:29) Which types of founders are they most interested in working with?
(18:01) Assessing the ethical implications of AI applications on caregiving.
(20:48) “The hardest decisions these founders might encounter might be many years after our capital has been put in.”
(23:36) Unsolved problems Courtney “would love to see” more founders focus on.
(28:23) Common misperceptions about AI and the care economy.
(30:43) Elana: “One area that we're interested in is memory care: Alheimer’s, dementia.”
(33:31) How to pitch Springbank VC.
(35:52) Tactical and strategic advice for first-time founders working on pitch decks.
(38:02) Elana: “I always really love when it is clear to me that founders have profound empathy.”
LINKS
Springbank VC
Elana Berkowitzelana@springbank.vc
Courtney Leimkuhlercourtney@springbank.vc
Carefull
Subscribe to Fund/Build/Scale
Apple Podcasts
Spotify
LinkedIn
Substack

Crafting influence: Early-stage PR strategies from Chikodi Chima of Moonshot

I interviewed Chikodi Chima, founder of Moonshot, a PR firm focused on early-stage startups. The discussion revolves around the art of storytelling, thought leadership, and how PR can exponentially boost brand presence and connect with media, along with prospective customers, employees and investors.
Chikodi shares insights from his journey as a former tech journalist to a PR professional, emphasizing the importance of creating compelling narratives and strategic influence for startup founders.
Key topics include understanding when to engage with PR, the role of media exposure, managing expectations about ROI, and avoiding common pitfalls in PR strategies. The conversation also touches on the significance of events and networking in enhancing brand credibility
“You can sell a problem long before you have a viable solution for it,” said Chikodi.
Runtime: 37:34
EPISODE BREAKDOWN
(2:09) How Chikodi transitioned from tech journalism into launching a PR agency.
(5:48) “How do I get people's attention, and how do I keep them involved in my story?”
(8:33) “If people see themselves in the story that the founder and the company is telling, they will get on board.”
(10:28) Moonshot's onboarding process for new clients.
(13:05) “I think of myself as a triple threat because I understand marketing, content events and PR.”
(16:52) “There's a lot of ways to get ROI out of events.”
(17:14) “A question that I get from founders a lot is, ‘how much time is this going to take from me?’”
(22:23) How he connects with new clients and sets expectations.
(25:54) “You really have to have something special, you have to be committed, you have to be resilient and you have to be adaptable.”
(29:15) “There is this sociopathic kind of tendency in certain founders, and you don't instantly recognize it.”
(33:10) “If you ask me, “when should we start doing PR,” I would say ‘yesterday.’”
LINKS
Chikodi Chima
@chikodi
Moonshot
The Key to Navigating Vulnerability at Work
Subscribe to Fund/Build/Scale on Substack
Thanks for listening!
– Walter.

From tech worker to tech founder: Lessons from Naveen Rao of Databricks

In 2014, Naveen Rao left his researcher job at Qualcomm to co-found machine intelligence platform Nervana. About two and a half years later, Nervana sold to Intel for more than $400 million.
After a few years at Intel, Naveen became CEO and co-founder of open source startup MosaicML, which helped companies build and train large AI models more efficiently and affordably.
Approximately two and a half years later, Databricks acquired that company for $1.3 billion and made him VP of Generative AI.
Naveen is a neuroscientist with multiple exits, so we spoke at length about shifting from engineering into entrepreneurship. If you have a technical role and are considering starting up, he shares his perspective on balancing day-to-day responsibilities while validating your idea, the importance of challenging industry assumptions, and finding your market niche. 
We also talked about who should — and should not — startup in stealth and addressed some of the current challenges facing the generative AI startup ecosystem, such as the rapid failure rates of companies due to high GPU costs and overinvestment in 2021-2022. 
Runtime: 51:16
EPISODE BREAKDOWN
(2:54) “Evidence is always less than you want. At some point you kind of have to take a leap.”
(5:37) “My journey with Nervana was, it was immediately clear to me that the world needed this.”
(11:52) “Get in the head of someone who's going to exchange money for your services and products.”
(14:54) Why he’s not a big fan of remote work.
(18:35) “It is on you as an adult to find balance that you can work with. It is not the company's duty to do this.”
(20:31) Why product companies should “probably not” startup in stealth.
(23:11) “It wasn't the right time to sell. I didn't look at it like that at all.”
(26:32) Hiring and retaining generative AI talent is “a hard problem right now.”
(30:16) “Companies are failing pretty fast because the GPU spends are so big.”
(35:04) Interacting with Databricks’ developer community.
(43:11) Naveen on accelerators: “I think there are actually faster ways to learn.”
(45:05) When it comes to angel investing, “I'm looking for creativity, honestly.”
(47:34) If you were interviewing for a job with an early-stage startup, what's one question you'd have to ask the CEO? 
LINKS
Naveen Rao
@NaveenGRao
Databricks
Databricks picks up MosaicML, an OpenAI competitor, for $1.3B
Intel is paying more than $400 million to buy deep-learning startup Nervana Systems
The Righteous Mind: Why Good People Are Divided by Politics and Religion, Jonathan Haidt
Ali Partovi
Subscribe to Fund/Build/Scale on Substack: fundbuildscale.substack.com
 

Unlocking growth-stage VC: Insights from CapitalG's Jill (Greenberg) Chase and James Luo

In July 2024, I visited the Ferry Building in San Francisco to sit down with CapitalG partners Jill (Greenberg) Chase and James Luo.
As Alphabet’s growth-stage VC fund, CapitalG specializes in backing startups that have found product-market fit and are ready to scale with investments ranging from $50M to $200M.
We talked about the key signals that indicate a company is ready for growth-stage investment, how CapitalG leverages Google and Alphabet resources to boost its portfolio, and their frameworks for assessing risk and potential returns.
We also spent time talking about the importance of go-to-market strategies, team-building, and product partnerships.
Whether you’re an early-stage founder or curious about what it takes to scale a business to the next level, this conversation offers actionable insights into navigating growth-stage funding.
Runtime: 53:05
EPISODE BREAKDOWN
(1:57) A general overview of CapitalG and its relationship to Alphabet and Google.
(6:11) What are some of the early signals indicating that a company is at growth stage?
(8:33) James: “When you get to the later stages, you have a ton of different data points that you don't have at the Series B.”
(12:53) Jill: “We talk a lot about the concept of, “are you paid for the risk that you're taking?”
(18:53) Jill: “Our job when things aren't going so well is to remind them of the dream and to say, ‘no, we're not giving up.’”
(19:30) Which trends and technology are Jill and James following these days?
(25:25) James’ framework for sizing TAM for growth-stage startups.
(30:50) James: “TAM is a judgment call. It's as much art as it is science.”
(32:28) Jill on what separates a high-potential AI startup from the rest of the pack.
(38:29) Jill: “The way we approach investing at CapitalG is highly thematic and sort of thesis-driven.”
(44:50) Why growth-stage investing is similar to park rangers looking for forest fires.
(48:45) James: “You're basically never going to find somebody who's amazing at every possible thing that you need to do to run a business.”
(51:01) Jill: “It is a huge red flag for me when somebody can't say, ‘yep, I was wrong about this.’”
LINKS
Jill (Greenberg) Chasejillgreenberg@capitalg.com
James Luo
CapitalGRobinhood
Stripe
Magic
Rippling
San Francisco Ferry Building

How Dovetail CEO Benjamin Humphrey scaled an Australian startup to global success

In this episode, Fund/Build/Scale host Walter Thompson interviews Benjamin Humphrey, CEO and co-founder of Dovetail, a customer insights hub based in Sydney, Australia.
They discuss the challenges of hiring for a bootstrapped company, early customer acquisition strategies, and the impact of local networking when starting up far from major tech hubs like Silicon Valley.
Benjamin shares his journey from being a lead designer at Atlassian to founding Dovetail, emphasizing the importance of building strong customer relationships and adapting products to solve real-world problems.
The episode also explores managing distributed teams, transitioning from bootstrapped to funded, and leveraging AI to enhance business operations. Lastly, Humphrey offers advice on maintaining focus and managing expectations in a startup environment, particularly for those starting up outside the traditional tech hotspots.
EPISODE BREAKDOWN
(03:26) How Dovetail’s customer insights hub works.
(05:14) “I’d always wanted to start a company.”
(9:19) “I got permission to basically start hacking on this little startup idea that I had in my spare time.”
(13:55) “We tossed around with the idea of co-CEO for a while.”
(14:24) “Being kind of at the arse end of the world means that you're forced into being this no-touch PLG business." 
(23:24) “The design team is the best-placed team to figure out what the holistic solution is that's gonna solve for the requirements of individual customers.”
(26:50) How he promotes a cohesive culture across widely distributed teams.
(30:01) Relocating teams between Sydney and SF, annual retreats.
(33:47) “We only started doing paid ads about six months ago.”
(36:28) “I'm actually our Australian sales rep at the moment.”
(39:10) How hiring challenges led Benjamin to revisit his stance against VC funding.
(43:40) Tall poppy syndrome is real in Australia, but “you just have to develop a thick skin as a founder.”
(48:29) “And then you realize if you start hiring people, you have to do management.”
(52:39) His future plans for Dovetail.
(56:30) How AI integrates into his vision for the company.
(1:00:26) What he’s looking for as an angel investor, final thoughts.
Runtime: 01:03:59
LINKS
Benjamin Humphrey
Dovetail
Blackbird VC
Atlassian
Just Ask!: 7 simple steps to unlock the power of clients, generate referrals and double your business, Graham Eisner
Why You Only Need to Test with 5 Users, Jakob Nielsen
Putting a Bolder Face on Google, The New York Times
Subscribe to Fund/Build/Scale
📓Substack: https://fundbuildscale.substack.com
🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/fund-build-scale/id1719488387
🎧 Spotify: https://open.spotify.com/show/0EbC8PTUSfpZ4USPC9ErnN
Thanks for listening!
– Walter.

Startup PR 101: Essential tips from SISU founder Jenna Birch

Jenna Birch is the founder of SISU, a PR firm that serves early-stage startups and VCs. She’s also a partner at Kaya Ventures.
We talked about how to recognize when it’s time to engage PR services, the importance of a founder’s personal branding and the path that led her from journalism into venture-backed tech.
She also shared her methodologies for assessing clients, setting realistic expectations, and creating impactful media strategies.
There are a lot of misconceptions around PR and comms, so I was glad to get her perspective on earned media, personal branding for founders, and tips for navigating the earlier stages of a startup's lifecycle with optimal PR strategies. 
“PR is not meant to make up for a lack of something in your business, it can't fix the thing that you really need to fix, for instance, finding product market fit,” she said.
“PR is not the gateway to do that. You have to have that figured out before you get PR.”
We also talked about how to interview a comms firm, her ballpark estimates for monthly fees, and which red flags to look for when a PR professional wants to rep you.
“You want to learn everything you can. So I'd also just ask about the transparency and how they're going to guide you through, because I think having a look behind the curtain — having someone that's willing to give you that look — is important.”
43:46 minutes
 
EPISODE BREAKDOWN
(1:55) “SISU is a very good startup word. It means ‘enduring grit.’”
(4:14) Her transition from journalism into being a comms professional/VC.
(7:26) Inside the process Jenna uses to assess potential clients.
(8:55) “PR is not meant to make up for a lack of something in your business.”
(12:08) SISU’s onboarding process: “I like to craft things in three-month sprints.”
(14:47) “Ultimately, you're the steward of your company's story. So I need you to be involved in that process.”
(19:14) How founders can identify/leverage news hooks and trends.
(22:10) When it comes to thought leadership, “most founders and most investors are not immediately good at that.”
(24:59) Why she thinks LinkedIn is more valuable than Twitter/X for business leaders.
(27:32) Which signals and metrics indicate you should hire outside PR help?
(31:16) The framework she uses to decide whether your startup is ready to hire her.
(32:27) “Anyone that promises you press is probably not the right partner for you.”
(35:05) Jenna ballparks a monthly cost for professional PR services.
(38:10) How she became a partner at Kaya Ventures/how to pitch her.
LINKS
Jenna Birch, founder, SISU
SISU
Kaya Ventures
NFX
Paid vs. Owned vs. Earned Media: What’s the Difference? (Harvard Business School)
Subscribe to Fund/Build/Scale
📓Substack: https://fundbuildscale.substack.com
🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/fund-build-scale/id1719488387
🎧 Spotify: https://open.spotify.com/show/0EbC8PTUSfpZ4USPC9ErnN
Thanks for listening!
– Walter.