Leary argues that community must be part of a company's behaviour from the beginning rather than a later promotional feature. Founders should participate as early members, explain the mission, invite users to help shape the product, and visibly act on their feedback so involvement feels genuine.

Authenticity is the foundation of a durable community
The founder or founding team should participate directly
Members should be treated as collaborators rather than distribution channels
Ignoring feedback weakens the trust the community depends on
Leary credits early Nextdoor members with materially shaping the product

“it should be a part of what you're doing from the very beginning”
Sarah Leary · 39:30

“it has to be part of the dna of the company”
Sarah Leary · 41:00

#community#authenticity#product

Hot Take53:30

Disruption Creates Windows for New Companies

Leary argues that major changes in how people live and work create openings for entrepreneurs to build new products. She connects those openings with a larger pool of capable builders and available capital, while noting that funding still depends on the quality of the idea.

Changed behaviour can expose needs that older products do not serve
Leary says more people had the skills needed to start companies
She viewed remote work and lifestyle change as sources of new opportunity
Her positive assessment is an entrepreneurial interpretation, not a guarantee of success

“disruption happens when disruption happens i think entrepreneurs see that there's an opportunity for something new to be created”
Sarah Leary · 53:30

#disruption#opportunity#innovation

Explainer· 1

Explainer43:00

How Declining Institutional Trust Raises Community's Value

Leary describes a broad shift away from trust in large institutions and toward grassroots recommendations. In her view, this makes authentic advocates increasingly valuable across consumer, software, enterprise, infrastructure, and open-source markets, because peers can explain how a product works in context.

Leary presents lower institutional trust as a macro trend
Peer recommendations can carry more weight than centralized promotion
Advocacy cannot be manufactured if users do not believe in the product
Community dynamics also appear in enterprise and open-source buying decisions

“we are increasingly less trustworthy uh trusting i'm sorry less trusting of large institutions”
Sarah Leary · 43:00

“you can't convince people to be advocates for your product your brand if they don't actually feel that way”
Sarah Leary · 43:30

#trust#word of mouth#community

Story· 4

Story01:30

Why Sarah Leary Kept Moving Toward the Earliest Stage

Leary traces her interest in entrepreneurship to a family filled with small-business owners, including her grandmother. Working on the first launch of Microsoft Office and later joining a startup as its fifteenth employee strengthened her desire to build companies from the ground up.

Entrepreneurship felt normal because it was visible throughout her family
Microsoft showed her the scale founders could create
Joining an early startup still left her wanting to begin at day zero
Her first startup later went public and was acquired by eBay

“i just wanted to go early stage”
Sarah Leary · 03:00

#career#entrepreneurship#startups

Story06:30

Fanbase Failed, but the Investor Backed the Team Again

After engagement, retention, and usage suggested Fanbase was not becoming a major sports community, Leary and her co-founder offered to return the remaining capital. She says their original investor declined, framed returning the money as the easier exit, and gave the reduced team a few months to search for a new direction.

The company still had roughly seven million dollars when the founders raised the issue
Leary says a couple of million dollars had been spent by then
The founders felt responsible for telling investors the original mission no longer looked viable
The investor's confidence created both runway and pressure to find a stronger idea

“we actually went back to our original investor and offered to give the money back”
Sarah Leary · 07:30

“i bet on the team”
Sarah Leary quoting the investor · 07:30

#failure#investors#pivot

Story08:30

The Everyday Connection Gap That Inspired Nextdoor

The Nextdoor concept grew from Leary's observation that people could connect globally on Facebook and professionally on LinkedIn while barely knowing nearby neighbors. The contrast with how she remembered growing up made the missing local layer feel like an opportunity worth exploring.

Existing networks served global and professional relationships
Nearby relationships remained comparatively underserved
The idea began in the founders' own experience rather than a technology trend
Early neighborhood conversations suggested others felt the same gap

“we didn't know the people who lived right next door or right down the street from us”
Sarah Leary · 08:30

#nextdoor#local#origin story

Story46:30

Why Leary Left Nextdoor's Operating Team for Venture Capital

As Nextdoor approached 400 employees, Leary faced a personal choice about committing to another three or four years of expansion and revenue growth. She moved to the board and joined Unusual Ventures because helping founders during company creation and product-market-fit work felt more energizing than operating the next phase of a larger organization.

The decision was about fit with Nextdoor's next stage, not a claim that the company was failing
Leary moved to the board rather than severing her connection
She wanted to return to early company creation
Her Fanbase and Nextdoor experience became practical guidance for other founders

“did i want to sign up for the next three to four years for the next phase of the company”
Sarah Leary · 47:00

“i was excited about sitting down with entrepreneurs in the early stages of their creation process”
Sarah Leary · 47:30

#career transition#venture capital#nextdoor

Q&A· 1

Q&A49:00

Nextdoor's Reported Scale and Advertising Model in 2021

Leary says Nextdoor sold feed advertising to local and large businesses but, as a privately held company, did not disclose revenue. She reported roughly 260,000 neighborhoods and tens of millions of users globally, while attributing increased use during the pandemic to demand for local information.

The stated revenue model included feed advertising for local and large businesses
Leary did not provide revenue figures
She reported about 260,000 neighborhoods worldwide
She described the user base as tens of millions
The scale and growth figures are the guest's contemporaneous claims from 2021

“we have the ability for local businesses large businesses to be able to advertise uh in in the feed”
Sarah Leary · 49:00

“tens of millions of users around the globe”
Sarah Leary · 49:30

#nextdoor#business model#scale

Takeaway· 1

Takeaway54:30

Choose Cofounders and Investors for the Full Journey

Leary's closing advice is to evaluate cofounders, team members, and early investors as long-term working partners. Complementary skills matter, but so do enjoyment, resilience through difficult periods, relevant expertise, and the ability to add something beyond capital; she says Nextdoor did not always optimize financing decisions for price and valuation.

Startup journeys can last five to ten years
Cofounders should combine complementary skills with strong working relationships
Early investors become part of the team through both good and difficult periods
Domain or stage expertise can be more useful than capital alone
Leary says Nextdoor prioritized partner quality over always maximizing valuation

“you want to pick people who are complementary to your skill set”
Sarah Leary · 55:00

“we didn't always optimize for price and valuation”
Sarah Leary · 55:30

#cofounders#investors#team

Frameworks in this episode

Big-Idea Opportunity Scorecard

Founding Champion Community Seed

Manual-to-Scale Learning Loop

Paired Idea Discovery Sprint

Problem-Before-Product Validation Gate

Insights & moments

◆Hot Take· 2

Why Community Cannot Be Bolted On After the Product