Unicorn Builders

By FrontLines.io

Learn from GTM journeys of B2B tech founders who’ve built companies worth more than $1 billion. This show is brought to you by FrontLines.io... more

· Business

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FAQs about Unicorn Builders:

How many episodes does Unicorn Builders have?

The podcast currently has 81 episodes available.

Unicorn Builders episodes:

January 16, 2026How Zocdoc survived near death, increased prices up to 100x, and turned around the company | Oliver Kharraz
Zocdoc has transformed healthcare access in America, powering one in three new doctor-patient relationships in New York City alone. Founded 18 years ago by physician Oliver Kharraz, the company nearly died 10 years in when it was growing just 1% annually and losing money on every customer. The pivot from subscription to pay-per-booking required raising prices 10-100x for existing customers, changing federal and state laws, and rebuilding core infrastructure - all while the sales team stopped acquiring new business to convert the existing base. Oliver shares the brutal mechanics of that turnaround, why nearly all churned doctors eventually returned, and how Zocdoc is now expanding beyond its marketplace with AI-powered tools like Zo, their voice assistant that eliminates hold times by handling unlimited simultaneous calls.
Topics Discussed:
The near-death experience 10 years in: barely 1% growth, negative unit economics, months of runway remaining
Managing thousands of emotionally charged conversations with doctors facing 10-100x price increases
Why Oliver paused the New York rollout mid-execution after creating a burning platform with employees
The strategic decision to target hardest-to-book specialties (primary care, OBGYN, dermatology) over acquisition-hungry cosmetic surgeons
Managing tens of millions of sub-markets defined by neighborhood, specialty, and insurance combinations
Transitioning from founder-led sales to enterprise motion while maintaining founder involvement 18 years later
Going on offense: powering insurance directories, embedding in Google and Apple Maps, launching Zo AI voice assistant
...more
31min
January 12, 2026How Augment Code achieved 80%+ win rates | Matt McClernan
Augment Code is pioneering AI tooling for professional software developers in enterprise environments. The company has built infrastructure that understands complex codebases better than individual developers, targeting a massive market undergoing fundamental transformation. In this episode of Unicorn Builders, I sat down with Matt McClernan, CEO of Augment Code, who joined as CRO in November 2024 and transitioned to CEO in July. Matt shares how Augment carved out differentiation in an explosively hyped market, achieved an 80%+ competitive win rate, and why the biggest competitors might actually be validating their market opportunity.
Topics Discussed
The decision to join Augment as CRO in a crowded, hype-filled AI coding market
Building ICP definition and sales process from scratch in the first 90 days
Achieving 80%+ win rates in competitive scenarios by focusing on complex codebases
Navigating "coopetition" with frontier labs (Anthropic, OpenAI) similar to hyperscaler dynamics
Hiring mission-driven sellers willing to embrace risk and uncertainty Understanding enterprise
AI adoption phases across Fortune 100 to tech startups
Transitioning from CRO to CEO and the personal growth required
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Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io
The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co
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Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.
Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM
...more
22min
January 12, 2026How Fireflies to Scaled to 700K organizations without touching any Series A Money | Krish Ramineni
Fireflies.ai reached unicorn status through a tender offer in 2024 — without raising primary capital since their Series A five years earlier. The company serves 700,000 organizations and reaches tens of millions of users monthly through meeting bot distribution. In this episode of Unicorn Builders, I sat down with Krish Ramineni, Co-founder & CEO of Fireflies.ai, to explore how the company rebuilt their entire product around LLMs in eight weeks, the brutal economics behind scaling PLG infrastructure, and why they're hiring TikTok creators over traditional B2B marketers as they prepare to expand beyond the meeting assistant category.
Topics Discussed:
The November 2022 inflection point when early GPT-3.5 access transformed product quality overnight
Building to unicorn status without touching Series A capital—funding entirely from seed round revenue
The infrastructure costs of supporting millions of users across AI processing, speech-to-text, and voice at PLG scale
Vertical product strategy: deploying domain-specific speech models, summaries, and integrations for healthcare, finance, and VC use cases
Marketing evolution from four years of zero spend to founder-led content and hiring consumer creators instead of B2B marketers
Distribution mechanics: viral loops from bots joining tens of millions of meetings monthly across 100+ countries
Category expansion beyond "AI note taker" into a 5x larger addressable market in 2026
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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io
The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co
//
Don't Miss: New Podcast Series — How I Hire
Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM
...more
32min
January 12, 2026How Plantd identified business process inefficiencies as a competitive wedge in building materials | Nathan Silvernail
Plantd is reinventing engineered lumber by replacing trees with rapidly renewable biomass, scaling manufacturing technology that costs 100x less than traditional OSB production. With customers including DR Horton and growing demand across furniture, RV, and international markets, Plantd has attracted partnerships throughout the building materials industry. In this episode of BUILDERS, I sat down with Nathan Silvernail, Co-Founder & CEO at Plantd, to explore how his decade at SpaceX shaped his approach to building a capital-intensive hardware company that could transform the $65 billion engineered lumber market.
Topics Discussed
Building continuous OSB production systems versus $500M batch presses used by incumbents
Securing DR Horton, furniture manufacturers, and building material companies as early customers
Managing the bifurcation between OPEX-intensive manual processes and CAPEX transitions to AI robotic vision systems
Designing machines for 400,000 panels/year output with sub-one-year payback at scale
Navigating opinion-based building inspection processes where "no two blocks in this entire country build a house the same way"
The strategic calculus of positioning away from climate tech to avoid green premium assumptions
Scaling from pilot production to deploying 25-30 machines to meet current demand pipeline
Achieving 70-layer panel construction versus 6-8 layers in timber-based OSB
...more
24min
January 07, 2026How Octane scaled to $400M revenue using small marketing teams that support partner brands instead of building their own
Octane Lending operates in what most VCs would consider an "unfundable" market - powersports financing for motorcycles, ATVs, and UTVs. Yet Jason Guss and his team have built a profitable unicorn that originated over $6.5 billion since inception, is on pace for $2.2 billion in originations this year, and generated $400+ million in revenue with $29 million in GAAP net income. In this episode of Unicorn Builders, Jason Guss shares how Octane leveraged being dismissed by 95% of investors as a competitive advantage, evolved from a failed marketplace to a successful lender, and is now pioneering "Captive as a Service" to reach their ambitious goal of $10 billion in annual originations by 2030.

Topics Discussed:
Octane's pivot from failed lending aggregator to successful direct lender
Building profitably in a VC-unfriendly market category (fintech lending)
The strategic advantage of competing against financial institutions rather than venture-backed startups
Evolving from speed and credit advantages to comprehensive end-to-end solutions
Launching "Captive as a Service" to white-label lending infrastructure for merchants and manufacturers
Navigating the 2021-2023 market correction while maintaining profitability
Long-term strategy for market expansion beyond powersports into auto and other recreational verticals

GTM Lessons For B2B Founders:
Embrace being in an "unfundable" market as a competitive moat: Jason intentionally chose a market that 95% of VCs dismiss, explaining "I compete primarily against financial institution incumbents. I don't have to compete with other venture backed businesses." While this meant less access to capital and higher bars for fundraising, it eliminated the "race to the bottom" competition common in hot VC markets. B2B founders should consider that being in an overlooked market can provide sustainable competitive advantages if the TAM is large enough to support venture outcomes.
Build for profitability from early stages when capital access is limited: Octane maintained profitability plans from Series B onward, with Jason noting "we always had a plan that would work since our Series B, that if we never raise a dime again, we'd be fine." This wasn't about never raising again, but ensuring they could "control their own destiny." B2B founders in less popular markets should prioritize unit economics and profitability early to reduce dependency on external funding cycles.
Expand value proposition beyond core product to create switching costs: Octane evolved from just offering faster credit decisions to providing "lead management tools, content strategy, workflow tools, to the financing and lifecycle marketing." Jason emphasized that "the SaaS product is much weaker without the lending attached to it" and vice versa. B2B founders should look for adjacent problems in their customers' workflows that they can solve to create a more comprehensive, harder-to-replace solution.
Partner with distribution channels that have aligned incentives: Rather than building direct-to-consumer, Octane focused on B2B2C through manufacturer partnerships. Jason explained they partnered with manufacturers "who knew that they were losing sales" and saw Octane as driving "extra sales." B2B founders should identify channel partners who have clear, aligned incentives for their success rather than trying to convince neutral parties.
Use early product criticism as competitive fuel: Jason candidly shared "originally, our product was awful and we got tons and tons of negative feedback. But guess what, that negative feedback was absolute gold because we listened to it and we just kept making our product better." The key was having distribution partners (merchants and manufacturers) who were incentivized to provide honest feedback because Octane's success drove their sales. B2B founders should structure early partnerships where customers have skin in the game and will provide brutal, actionable feedback.
Plan strategic evolution in 2-3 year waves rather than 10-year master plans: Jason described their approach as finding "something that's really underserved or an opportunity that we think is exciting" and riding "that wave as long as we can. And as we see the wave is petering out, we try to find the next mountain to climb." Their waves included: 1) speed and superior credit (2016-2018), 2) end-to-end purchasing tools (2018-2022), and 3) Captive as a Service (2022+). B2B founders should focus on medium-term strategic planning while remaining flexible about long-term direction.

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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership.
www.FrontLines.io

The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.
www.GlobalTalent.co
...more
32min
November 26, 2025How Dataiku serves 700+ enterprise customers by becoming the AI governance layer | Florian Douetteau
Florian Douetteau founded Dataiku in 2013 with a contrarian thesis: enterprise AI transformation must come from business operators, not centralized data science teams. While Silicon Valley built for tech companies, Dataiku built the translation layer between fragmented IT infrastructure and the business users who understand actual enterprise processes. With over $850 million raised, $350 million in ARR, and 700+ enterprise customers including 25% of the Fortune 500, Dataiku positioned itself as the permanent infrastructure layer—the glue that remains stable while data platforms churn every 2-3 years. In this episode of Unicorn Builders, Florian explains why retention comes from AI project velocity rather than platform stickiness, how they compete by sitting above infrastructure vendors like Snowflake and Databricks, and why the "GPT-8 will solve everything" worldview fundamentally misunderstands enterprise requirements.
Topics Discussed:
Why democratizing AI for business operators beats centralized data science teams in enterprises
Dataiku's buyer persona: the "in-between" leader managing AI strategy between IT and business
How avoiding professional services enabled platform-led growth to Fortune 500 scale
Competing with Snowflake, Databricks, and Microsoft Fabric by positioning as the translation layer
Why enterprise IT infrastructure changes every 2-3 years—and how that creates permanent demand for glue
Measuring retention through AI project velocity instead of platform usage metrics
Building from France while recruiting experienced executives from US public companies
The workforce shift: from 80% transacting to 80% inspecting automated systems
Why enterprises need "reasoning layers" that encode business logic into automated systems
The Faustian bargain of agents: uncoordinated AI creating organizational chaos at machine speed
Data sovereignty vs. EU AI Act: two fundamentally different regulatory challenges
Why governance must be built into AI projects from inception, not bolted on at the end
Florian's 12-year relationship with the same buyer persona and why founder-market fit spans decades
GTM Lessons For B2B Founders:
Target the structural "in-between" role that bridges technical and business worlds: Dataiku's buyers aren't CTOs managing infrastructure or business leaders focused purely on outcomes—they're "people sitting most of the time in IT, but very much business focused" who run AI strategy, analytics, and data initiatives. These leaders face a permanent structural problem: fragmented infrastructure that changes every 2-3 years on one side, business users demanding project delivery on the other. Most vendors optimize for one side; nobody built for the translation layer as the primary product. B2B founders should identify these permanent structural gaps that exist regardless of which specific technologies are in vogue.
Platform architecture beats professional services for enterprise scale: When business users couldn't apply AI, the obvious path was high-margin consulting. Dataiku rejected this explicitly: "We actually managed very well to avoid, I would say this consulting trap" by building training, partner ecosystems, and self-service capabilities instead. Two years later, this enabled them to sell to US Fortune 500 companies—a jump requiring platform sophistication for customer independence, not dependency. The strategic bet: self-service drives faster adoption and better retention than services. Founders should design for customer capability-building from day one, even in complex domains.
Retention through output velocity, not platform stickiness: Most enterprise software tracks NRR or feature adoption. Dataiku measures "the acceleration and the multiplication of AI projects"—how many production deployments business teams deliver. Florian was explicit this differs fundamentally from traditional retention: "Retention is not built out of thin air or being just a virtue of being perceived as indispensable...retention is derived from the business value you generate." Each successful project creates organizational capability for the next one—teams delivering five projects become equipped to deliver ten, then twenty. The platform becomes valuable through accumulated competency, not technical lock-in. Founders should define success metrics that create compounding customer capability rather than switching costs.
Position as infrastructure that outlasts technology churn: Rather than competing feature-for-feature with Snowflake and Databricks, Dataiku positioned as the stable layer above constantly-evolving infrastructure. Enterprise data ecosystems "very candidly change every two or three years"—Hadoop to cloud to Snowflake to Databricks, with new platforms constantly emerging. Infrastructure vendors will "always optimize for technical capabilities, not business user experience." That permanent gap between infrastructure sophistication and business accessibility is Dataiku's sustainable position. Every platform shift reinforces the need for translation infrastructure. Founders should find the layer that remains stable while underlying technologies fragment.
Build global leadership for scale while maintaining technical centers of excellence: Dataiku kept product and engineering in France but recruited experienced executives globally from proven US public companies. "A lot of the people with the experience of scale and the experience of speed have got this experience in the largest U.S. companies," Florian explained, noting their team includes leaders from Zoom, ServiceNow, and Twitter—companies that successfully navigated public markets at scale. This hybrid model maintained technical excellence in their original base while accessing operational expertise required to sell enterprise software where Fortune 500 buying decisions happen. European founders shouldn't choose between staying local or relocating entirely—build hybrid structures that capture both advantages.
Choose customer personas for decade-long relationships, not quick wins: Before starting Dataiku, Florian received advice that if he succeeded, he'd "be there for 10 years or 15 years or 20 years," meaning "you really need to love this persona because it's a very long relationship." Twelve years later, he still serves the same buyers: "I love the person I'm serving, meaning the AI, data, science, data people, the people that are in between in the business." This wasn't sentimentality—building enterprise infrastructure means decade-long customer relationships that become exhausting if you don't genuinely connect with your persona. Founders should select buyers they can authentically engage with long-term, as the relationship will define their career trajectory.
Let category positioning evolve through customer feedback rather than forcing premature definition: Dataiku's positioning evolved organically from "data science platform" to "enterprise AI reasoning layer" as customer needs clarified over years. They didn't force category creation upfront—it emerged from solving actual problems at scale. The key was staying close enough to customers that positioning refined naturally rather than remaining locked into initial positioning that missed the market. Founders should prioritize solving real customer problems and allow category language to develop through operational insights rather than predetermined marketing frameworks.
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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io
The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co
//
Don't Miss: New Podcast Series — How I Hire
Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.
Subscribe here:
https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM
...more
1h 8min
November 25, 2025Inside the Race to Build AI Infrastructure w/ Sheldon Kimber
Intersect is solving AI's fundamental constraint: gigawatt-scale power delivered outside traditional grid infrastructure. The company builds behind-the-meter renewable and gas generation paired directly with data centers in locations like West Texas, bypassing the Balkanized regulatory system that makes grid expansion nearly impossible. Currently constructing $9 billion in assets across multiple sites and breaking ground on $10 billion more in 2025, Intersect represents the emerging infrastructure layer that neither traditional utilities nor digital REITs can address. In this episode, I sat down with Sheldon Kimber, CEO and Founder of Intersect, to unpack how his finance-heavy background enabled a contrarian approach to the AI infrastructure buildout.
Topics Discussed:
Why the US grid's Balkanization across state, federal, and regional system operators makes it structurally unfixable
The business model shift from utility PPAs to operating in deregulated commodity energy markets
Intersect's hybrid model: flexible reciprocating engines and aeroderivative turbines paired with renewables
Why AI reasoning models and larger context windows guarantee sustained electricity demand growth despite efficiency gains
The capital formation playbook: hundreds of thousands for early development, billions in non-dilutive project finance post-contract
How single gigawatt data centers translate to $50-60 billion all-in infrastructure when accounting for power, shell, turnkey, and chips
The AI infrastructure stack battle: Neo clouds pushing down, power companies pushing up, and who owns the constraint
GTM Lessons For B2B Founders:
Design around regulatory arbitrage, not reform: Intersect's entire business model targets unregulated spaces. Sheldon rejected the conventional utility PPA path, stating: "We built a business model that is not go right at something." Their behind-the-meter, off-grid approach operates outside state public utility commissions, FERC jurisdiction overlaps, and ISO/RTO coordination failures. When entering regulated markets, map the jurisdictional gaps and build your product to live in those spaces rather than fighting for reform that won't come.
Bet on technological disruption of calcified systems: Sheldon explicitly compared the grid to the Bell System, which wasn't reformed but rendered irrelevant by cellular, fiber, and digital infrastructure. He observed: "Nobody inside the regulated telecom industry said, let's fix this. Brand new technologies just completely gutted it from the inside out." When facing entrenched infrastructure with misaligned incentives across fragmented stakeholders, identify the technological bypass rather than incremental improvements. The constraint that makes reform impossible also creates the asymmetric opportunity.
Optimize for project scale, not team expansion: Intersect maintains radical efficiency by building only gigawatt-scale projects with lean teams. Sheldon's framework: "It takes the same number of people in contracts to build a gigawatt plant as it does to build a hundred megawatt plant, so you might as well build the bigger one." This isn't generic "do more with less"—it's identifying which costs are fixed regardless of project size (legal, interconnection applications, permitting) versus variable (construction materials). B2B founders should analyze their own cost structure to find similar leverage points where deal size scales independent of resource requirements.
Lock major contracts before infrastructure deployment: Intersect's capital strategy starts with hundreds of thousands for land options and interconnection applications, uses early reputation to secure anchor contracts, then raises billions in non-dilutive project financing against those contracts. Sheldon described it as: "Making enterprise software where your first sale was to 10 Fortune 500s and they took everything you could possibly build for the next five years." The contract becomes the collateral for low-cost debt financing. For capital-intensive B2B models, structure early sales to de-risk the bulk of your capital deployment.
Identify where constraints migrate in your value chain: Sheldon analyzed the AI infrastructure stack from dirt to chips and concluded: "For the next decade, there'll be a constraint in the physical infrastructure. It'll need cloud providers that have access and expertise to build infrastructure and achieve capital formation around infrastructure." Value accumulates at bottlenecks. Neo clouds like CoreWeave started at the model layer and are pushing down; Intersect started at power and is pushing up. Position your product where the constraint is moving, not where it currently sits. This requires continuously modeling your industry's supply chain physics.
Let unit economics override industry narratives: While energy policy debates favor nuclear and central-scale combined cycle gas plants, Intersect's math shows their hybrid approach—flexible reciprocating engines and aeroderivative turbines with renewables and batteries—delivers power at a fraction of the cost. Sheldon noted alternatives run "$120-150 a megawatt hour versus most people paying $30-40." He emphasized: "It's just math and it's not hard math." Strip away conference circuit consensus and regulatory capture. Model actual delivered unit economics, then let superior economics compound into strategic advantage while competitors chase policy-driven narratives.
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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io
The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co
//
Don't Miss: New Podcast Series — How I Hire
Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.
Subscribe here:
https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM
...more
45min
November 05, 2025Why Cart.com spent $5 million on a domain name as their first marketing strategy | Omair Tariq
Cart.com achieved unicorn status in less than three years by pioneering a radically different approach to building a commerce enablement company. Rather than starting from scratch, founder Omair Tariq began with strategic acquisitions - nine companies in the first 14 months - to rapidly assemble the technological and operational infrastructure needed to help mid-market brands sell across multiple channels globally. With a current valuation exceeding $1 billion and revenue approaching half a billion dollars just four years in, Cart.com has created an entirely new category of vertically integrated commerce enablement that bridges venture capital growth with private equity acquisition strategies.
Topics Discussed:
Cart.com's unconventional founding strategy: acquiring companies before building organically
The challenge of assembling nine acquisitions in 14 months while building a cohesive company culture
Evolution of go-to-market strategy from end-to-end messaging to problem-specific approaches
The talent evolution challenge: transitioning from M&A specialists to company builders
Marketing strategy evolution from viral brand campaigns to targeted content and education
Revenue growth from $30M to $180M in year two through combined inorganic and organic growth
The decision to invest $5M in the Cart.com domain name as a credibility-building marketing strategy
GTM Lessons For B2B Founders:
Start with the customer's decision-making reality, not your product vision: Cart.com initially pitched their end-to-end commerce solution to CEOs, but discovered that mid-market companies have specialized decision makers. The CMO buys marketing services, the CLO buys logistics, and the CTO buys technology platforms. Omair learned to lead with specific problems for specific decision makers, then cross-sell the broader vision. As he explained: "When we came out with this end-to-end journey, the mid-market was just confused in terms of who would make that decision." B2B founders should map their solution to existing organizational buying patterns rather than expecting customers to change their decision-making structure.
Perfect your core offering before attempting cross-sells: Cart.com's biggest mistake was trying to cross-sell immature products to existing customers. When they sold Amazon marketplace services before the capability was fully developed, it damaged credibility for their core fulfillment offering. Omair spent months on "apology tours" to repair relationships. The lesson: "Our product and capabilities always have to catch up to our go-to-market motion... you oversell a little bit, but if you do too much of it, then you don't convince them." B2B founders should establish world-class performance in their initial offering before expanding the relationship.
Reinvent marketing when you're creating a new category: Traditional marketing tactics didn't work for Cart.com's unprecedented value proposition. Trade show booths and paid search ads couldn't communicate their vertical integration story. Instead, they hired marketers who could "invent the playbook" rather than apply existing frameworks. Their head of marketing succeeds because "he doesn't have a playbook, he invents the playbook." B2B founders building novel solutions need marketing talent comfortable with experimentation over expertise.
Use cross-sell timing as a competitive moat: Cart.com's current strategy involves spending 6-12 months delivering exceptional service in one area before introducing additional capabilities. This patience allows customers to organically request expanded services during strategic business reviews. Omair notes: "When you do the world's best job helping your customers, and they in the back of their mind know there's more you can do, they approach you themselves." This approach creates stronger customer relationships and higher success rates than aggressive early cross-selling.
Choose investors based on capital, terms, and understanding - not brand: Despite access to tier-one VCs, Cart.com prioritized three factors: maximum capital, best terms, and investor comprehension of their unique model. Omair was skeptical of young associates from large funds: "Do I really want this 26-year-old Stanford grad telling me how to build my company when he or she has never done that before?" For experienced founders, investor brand recognition matters less than practical support and strategic alignment.

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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership.
www.FrontLines.io

The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.
www.GlobalTalent.co
...more
36min
October 31, 2025How ClickUp survived the 2021 growth at all costs era and came out stronger ($300M ARR)
ClickUp is redefining workplace productivity by converging multiple software categories into one flexible platform. With over $400 million raised and a valuation exceeding $4 billion, ClickUp has grown from a bootstrapped internal tool to serving millions of users globally. In this episode of Unicorn Builders, I sat down with Zeb Evans, Founder & CEO of ClickUp, to explore the company's unconventional journey from ignoring Silicon Valley's conventional wisdom to building one of the fastest-growing productivity platforms in the world.
Topics Discussed:
ClickUp's origin as an internal productivity tool solving tool fragmentation
The decision to ignore venture capital advice about niching down and avoiding competitive markets
Building natural product-market fit through bootstrapping versus artificial growth through funding
The intense fundraising period of 2020-2021 that raised over $500 million in 18 months
The cultural challenges of hypergrowth and the return to "founder mode"
Transitioning from growth-at-all-costs to profitable, efficient operations
ClickUp's unique approach to performance marketing by hiring consumer-focused talent
The strategic decision to build headquarters in San Diego versus Silicon Valley
AI integration strategy focused on human productivity enhancement rather than replacement
GTM Lessons For B2B Founders:
Build for your own pain, but pivot quickly to market needs: Zeb emphasized that ClickUp started as an internal tool to solve their team's productivity fragmentation across 15 different tools. However, the key was recognizing within weeks that this was a broader market opportunity. B2B founders should solve their own problems first, but be ready to quickly assess whether their solution has wider market appeal and pivot accordingly.
Ignore conventional wisdom when you have conviction: Despite universal advice to "niche down" and avoid competitive markets, ClickUp deliberately built flexible software for teams of "two or more people" across all verticals. Zeb noted that everyone said "do not go into this category, this is so stupid," but their conviction about building flexible, customizable software that molds to how teams work proved correct. B2B founders should listen to advice but trust their instincts when they have deep conviction about their approach.
Bootstrap to natural product-market fit before raising: ClickUp remained profitable and bootstrapped until reaching $10 million ARR, which Zeb calls "natural product market fit rather than artificial product market fit." This approach forced them to build a truly valuable product without using dollars to mask product deficiencies. B2B founders should consider bootstrapping as long as possible to ensure genuine market demand before accelerating with external capital.
Hire performance marketers from consumer, not B2B: One of ClickUp's most counterintuitive moves was hiring their head of performance acquisition from the consumer side. Zeb explained, "the only people that figure out performance marketing at scale is in the consumer side... you can't even name them on a full hand if people had to figure it out on the B2B side." B2B founders should look beyond traditional B2B backgrounds when building growth teams, especially for performance marketing roles.
Focus on existing engaged users over new logo acquisition: ClickUp discovered that chasing big company signups was less effective than building relationships with users who were already actively using and paying for the product. Zeb noted, "it was really more about looking at the users that are already active users... go build relationships with those people. And then that's your foot in the door." B2B founders should prioritize expanding relationships with engaged users rather than constantly chasing new prospects.
Culture preservation requires intentional hiring alignment: During hypergrowth, ClickUp hired leaders with impressive backgrounds who weren't culturally aligned, leading to significant culture erosion. Zeb learned that "people just don't change" and that mixing people with fundamentally different work philosophies destroys culture. B2B founders must be explicit about cultural expectations during hiring and prioritize cultural fit over impressive resumes, especially during rapid scaling phases.

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Sponsors:
Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership.
www.FrontLines.io

The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.
www.GlobalTalent.co
...more
44min
September 11, 2025How Intercom survived by cannibalizing their own business model before competitors could | Des Traynor
Intercom is a pioneer in customer communication platforms, with $241 million in funding and serving thousands of customers worldwide. After 15 years of building horizontal messaging tools, the company made a dramatic strategic pivot in 2022 to focus entirely on AI-powered customer support. In this recent episode of Unicorn Builders, we sat down with Des Traynor, Co-Founder of Intercom, to learn about their remarkable transformation from a sprawling communication platform to an AI-first customer service leader—and how they shipped their first AI features just four weeks after ChatGPT's launch.
Topics Discussed:
Intercom's "five alarm fire" moment when ChatGPT launched and the immediate roadmap pivot
The painful but necessary decision to abandon multiple product lines and focus solely on customer service
How they developed outcome-based pricing for AI agents (charging per resolution vs. per seat)
The technical complexity behind building production-ready AI support tools beyond "thin wrappers"
Strategic lessons from the early competition with Drift and category positioning challenges
Why most B2B companies are reacting too slowly and superficially to the AI transformation
Building a sustainable company culture that retains talent for 15+ years
GTM Lessons For B2B Founders:
React with appropriate urgency to existential technology shifts: When ChatGPT launched, Des and the team immediately recognized it could eliminate their entire category. Within days, they "ripped up the roadmap" and went "hard on it." Four weeks later, they shipped their first AI features, and eight weeks later launched Fin, their AI agent. Des emphasizes this wasn't heroic—it was survival: "I don't know if I'm going to survive over here, but I'm not going to survive back there." B2B founders facing similar disruption should move with maximum speed rather than hoping for gradual adoption timelines.
Choose painful focus over comfortable sprawl: Intercom's decision to abandon their marketing and sales tools to focus solely on customer service was existentially difficult but critically necessary. Des explains they were "trying to bring too much software to market" and facing the challenge that enterprise buyers couldn't figure out who to talk to about their horizontal platform. The focus decision came from identifying where they had "the clearest right to win"—customer service had their happiest, stickiest revenue and most differentiated product. B2B founders should ruthlessly evaluate where they have the strongest competitive position rather than trying to serve every adjacent market.
Align pricing models with value delivery in AI transitions: Intercom moved from seat-based pricing to outcome-based pricing, charging roughly $1 per resolution. This required confidence that their AI actually works—Des notes "you should only charge for outcomes if you're definitely delivering outcomes." The pricing works because some customers find it "10x to 20x cheaper" than their current approach, while others struggle with the cost depending on their customer value. B2B founders implementing AI should consider how pricing models need to evolve to reflect the actual value delivered rather than traditional input-based metrics.
Embrace the innovator's dilemma decisively: Des argues most B2B companies are responding to AI with "delay" or "dilution"—either waiting another quarter or making meaningless changes. He advocates for completely reimagining products "from a blank page, as if it's 2025 and AI is here." The book he's writing addresses this challenge: companies must choose between building the product that kills them or dying of natural causes. B2B founders shouldn't hedge—they should assume AI capabilities will advance rapidly and rebuild accordingly rather than making incremental adjustments.
Build authentic thought leadership around your expertise: Intercom's marketing strategy centered on genuine knowledge sharing rather than typical B2B lead generation tactics. Des explains they wrote "everything that was true and stuff that we genuinely believed" about running B2B SaaS products, creating real value for their target market. Their current AI content follows the same approach—sharing practical insights about AI implementation rather than hype. B2B founders should focus on contributing genuinely valuable knowledge to their industry rather than optimizing for short-term lead capture.

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The podcast currently has 81 episodes available.