%20scale(0.03125,-0.03125)'%20d='M78%200V1760H782V1420H436V1077H768V746H436V343H805V0Z'%20fill='%23f5f1ea'/%3e%3cg%20transform='translate(29.22,37.12)'%3e%3cpath%20d='M0%200%20L9.244171875%200%20L30.81390625%2038.115828125%20L21.569734375%2047.36%20Z'%20fill='%23e8aa4e'/%3e%3cpath%20d='M0%2047.36%20L9.244171875%2047.36%20L32.48%204.87%20L25.94%20-1.67%20Z'%20fill='%23e8aa4e'/%3e%3cpath%20d='M36.98%20-6.16%20L32.60%2011.03%20L19.79%20-1.78%20Z'%20fill='%23e8aa4e'/%3e%3c/g%3e%3cpath%20transform='translate(71.39,84.48)%20scale(0.03125,-0.03125)'%20d='M62%200V1760H402V0Z'%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(88.77,84.48)%20scale(0.03125,-0.03125)'%20d='M229%200V1422H20V1760H790V1422H581V0Z'%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(116.96,84.48)%20scale(0.03125,-0.03125)'%20d=''%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(134.84,84.48)%20scale(0.03125,-0.03125)'%20d='M78%200V1760H555Q747%201760%20834.5%201666.5Q922%201573%20922%201358V1281Q922%201157%20877.5%201080.0Q833%201003%20742%20979Q861%20949%20901.5%20838.5Q942%20728%20942%20569Q942%20398%20910.0%20270.0Q878%20142%20794.0%2071.0Q710%200%20555%200ZM422%201097H494Q543%201097%20557.0%201135.0Q571%201173%20571%201226V1403Q571%201488%20496%201488H422ZM457%20310Q594%20310%20594%20440V660Q594%20735%20571.5%20778.5Q549%20822%20487%20822H422V312Q444%20310%20457%20310Z'%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(168.35,84.48)%20scale(0.03125,-0.03125)'%20d='M498%20-16Q287%20-16%20175.5%20111.5Q64%20239%2064%20480V1316Q64%201542%20174.5%201659.0Q285%201776%20498%201776Q711%201776%20821.5%201659.0Q932%201542%20932%201316V480Q932%20239%20820.5%20111.5Q709%20-16%20498%20-16ZM501%20308Q581%20308%20581%20463V1322Q581%201452%20503%201452Q415%201452%20415%201319V461Q415%20379%20435.0%20343.5Q455%20308%20501%20308Z'%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(202.35,84.48)%20scale(0.03125,-0.03125)'%20d='M30%200%20200%201760H797L964%200H631L606%20284H394L372%200ZM419%20565H579L502%201460H486Z'%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(236.30,84.48)%20scale(0.03125,-0.03125)'%20d='M78%200V1760H618Q753%201760%20822.0%201698.5Q891%201637%20914.5%201526.5Q938%201416%20938%201267Q938%201123%20901.5%201037.0Q865%20951%20764%20918Q847%20901%20880.5%20835.5Q914%20770%20914%20666V0H567V689Q567%20766%20535.5%20784.5Q504%20803%20434%20803V0ZM436%201108H521Q594%201108%20594%201267Q594%201370%20578.0%201402.0Q562%201434%20518%201434H436Z'%20fill='%23f5f1ea'/%3e%3cpath%20transform='translate(269.68,84.48)%20scale(0.03125,-0.03125)'%20d='M78%200V1760H562Q752%201760%20848.0%201654.5Q944%201549%20944%201346V522Q944%20272%20856.5%20136.0Q769%200%20550%200ZM432%20311H493Q590%20311%20590%20405V1313Q590%201401%20566.5%201426.5Q543%201452%20471%201452H432Z'%20fill='%23f5f1ea'/%3e%3c/svg%3e)
The $100M Exits Podcast
Jason Kirby sits down with the founders, operators, and investors behind nine-figure outcomes. No fluff, no theory — just the decisions, numbers, and mistakes that decided the exit.
Founders scaling past $10M
Hear how peers navigated the exact bottleneck you're in now.
Founders eyeing an exit
Valuation, diligence, and deal terms explained by people who closed them.
Operators & investors
Pattern-match across 100+ nine-figure companies in one place.
The complete archive, 124 episodes. Search by guest, topic, or anything said on the show.
After scaling his family's liquor empire to $100M and selling it to private equity, Brian Rosen left an estimated $10M on the table due to critical deal structure mistakes. Now managing InvestBev, a $300M fund, he reveals how he manufactured a second $20M+ strategic exit and why his investment thesis is to bet on founders over ideas in the non-correlated alcohol industry.
Growth equity targets capital-efficient companies with product-market fit, offering founders a path to scale and take chips off the table without the binary risk of VC. Jim Ferry of Volition Capital ($1.8B AUM) explains how his firm structures minority deals and why, in today's market, being "AI-native" is the key differentiator between premium M&A multiples and getting stuck in the valuation gap.
The US venture capital system is broken, forcing companies to stay private longer and build massive preference stacks, argues Jeff Stewart. He makes the case that for companies doing "$10, $20 million, $50 million, $100 million in revenue," a global IPO offers a superior path to evergreen capital, M&A currency, and talent, bypassing the limitations of the US mega-cap market.
For family-owned businesses, standard M&A can be tricky. Drew Allen of Grace Technologies shares two creative deal structures—a technology holding company and a sales-based equity earn-out—to acquire technology and incentivize key talent without giving up family ownership.
Speyside Equity partner Eric Wiklendt breaks down the private equity playbook that grew a manufacturing company from $7.8M to over $100M in EBITDA in seven years. Discover how their "fix and build" strategy involved shutting down 17 of 26 plants and divesting two entire divisions to unlock a 10x outcome without relying on high leverage.
After a multi-million dollar exit, founders often make critical mistakes like trying to time the market, underinvesting in themselves, and overestimating their skills as angel investors. Sriram Gollapalli, who sold his bootstrapped SaaS company iLabs to Agilent, reveals the psychological and financial traps that ensnare newly wealthy entrepreneurs and why finding a trusted peer group is the most crucial next step.
After getting "ripped off" in his first M&A deal, Dipak Patel learned a hard lesson about advisor selection and asset valuation. He applied that discipline to scale his next company, NAO, to $132M in revenue by mastering enterprise sales with a unique "cookie strategy" and a powerful referral engine.
Daniel Rosenberg sold his creator merchandise platform, Represent, for $100M to Custom Ink, then spun it out for a second exit to Cameo. He reveals how a fundraising process turned into a strategic acquisition, the critical founder mistake made during a 9-month diligence, and why a "1+1=3" M&A thesis can fail during post-acquisition integration.
Defense tech startups succeed by solving specific warfighter needs, navigating a complex DoD sales cycle, and building assets that attract strategic acquirers. Scout Ventures GP Bradley Harrison breaks down the playbook, citing the $100M+ exit of Tomahawk Robotics, which was acquired for its core tech, engineering talent, and a key $52M Marine contract that gave the buyer access to all five military branches.
For founders seeking growth capital without significant dilution, George Alifragis of Metropolitan ($1.8B AUM) explains how bespoke private credit can fund a company from a Series A to D-equivalent stage. He details how flexible, non-controlling capital from $10M-$100M can be structured as debt but behave like growth equity, preserving founder ownership while fueling scale.
Serial founder Jess Mah argues that AI has created an existential crisis for established tech companies, where even unicorn founders feel 'on the verge of a panic attack.' To survive, she advises founders to get their hands dirty again by building a new AI-native side hustle to $1M ARR themselves, proving they can still compete with the speed of today's 22-year-old YC grads.
After raising $20M for DTC sneaker brand Koio, Chris Wichert faced a market collapse and a -$3M EBITDA. He shares the tactical playbook for cutting 70% of his team and 40% of SKUs to turn the company profitable and engineer a successful exit against all odds.
Brian Ree grew DTC brand Daily Look by relentlessly focusing on a $500 customer LTV, which led to a merger with Adore Me and a subsequent $700M acquisition by Victoria's Secret. He reveals how a near-bankruptcy event forced a pivot from a $0 to a $40 styling fee, a move that lost 40% of customers but ultimately saved the company and defined its premium market position.
Sendoso founder Kris Rudeegraap raised a $100M round from SoftBank in late 2021, but just months later, the "growth at all costs" mandate evaporated. He explains the whiplash of pivoting to efficiency and how he deployed capital to acquire two competitors instead of just hiring hundreds of SDRs.
After his first multi-million dollar business collapsed in the 2008 crisis, James Rose had to swallow his pride and take an entry-level sales job. He shares the brutal lessons from that transition and how it shaped his current strategy of acquiring profitable agencies to build a holding company for a larger private equity exit.
Most VCs operate from a “prevention” mindset (fear of loss) rather than a “promotion” mindset (focus on upside), explains investor and VC advisor Aram Attar. He breaks down the psychology that drives investor decisions and internal investment committee politics, using a 20-year journey to a $3.5B public company as a case study on overcoming the sunk cost fallacy.
At 22, Matthew Wyatt bootstrapped a software company to over $100M in sales with a relentless sales culture, but a series of catastrophic failures—including a rogue partner, internal fraud, and a $400k/month cash burn—forced him to liquidate the business. This is a cautionary tale of losing focus, the danger of misplaced trust, and the hard-won lesson to "trust but verify."
With no defense tech background, Nelson Mills raised $76M in two years for VATN Systems by aligning with a VC's thesis and relentlessly building a customer-driven product. He reveals how he raised a $60M Series A by proving production revenue and why hiring a lobbying firm on day one is non-negotiable for winning government contracts.
After building fintech unicorn Clearco, Andrew D'Souza raised an $8M seed round for his new venture, Borty.ai, when the AI itself cold-pitched an investor whose 'mind was blown.' He explains why AI-driven, high-trust introductions are replacing the traditional warm intro and how Borty aims to be involved in 90% of active fundraises within a year.
After bootstrapping eSkill for 20 years, Eric Friedman sold his company and accepted a deal with an earnout, only to be removed as CEO and lose control over the outcome. He warns founders to treat earnouts as a bonus they will likely never receive and to evaluate the upfront cash portion as the true value of the deal.
Greg Brogger, founder of SharesPost, details his $160M exit to competitor Forge Global—a deal forced by a COVID-era market crash that derailed his Series D. He reveals the playbook behind a clever $15M joint venture with NASDAQ and why creating a financial "floor" is the most critical, overlooked strategy for founders.
To find top startups, DreamIt Ventures pivoted from a generalist pre-seed model to a later-stage program focused on enterprise sales, filtering for founders who understood the value of customer introductions over small checks. Andrew Ackerman reveals the playbook, including the unique deal structure that served as an "intelligence test" to separate sophisticated operators from the rest.
Ron Reiter reveals the raw psychology of his $50M exit to Oracle, where founder fear and imposter syndrome drove them to accept the first offer against their VCs' advice. He explains the M&A tactic that got Oracle's term sheet in three days and contrasts this fearful mindset with the "unfair advantage" he used to raise over $100M for his next company, Centra.
Crisis management isn't about having a playbook; it's about building trust with stakeholders *before* the unexpected happens. Crisis expert David Meadvin shares stories of near-miss IPOs and CEO blunders to reveal a framework for making calm, fact-based decisions when a deal, financing, or your reputation is on the line.
Thunder co-founder Oliver Low shares his founder M&A playbook, detailing the difficult exit of his ad-tech company, Platform 360, and why he believes 9 out of 10 earnouts are designed to fail. He provides a tactical guide to modern deal structures, including the rise of private equity buyers and how founders can leverage consolidation and buy-side strategies to engineer massive outcomes.
Itamar Novick, Managing Partner at Recursive Ventures, details his decision to bet his entire net worth to buy into Life360, a move that culminated in an $8B NASDAQ-listed company. This episode unpacks the grit required to survive near-bankruptcy, the strategy behind raising a pivotal $17M Series A, and the logic of pursuing a dual-IPO path starting in Australia to manage a complex cap table.
Max Buchan raised $20M for Valarian by proving deep tech market fit through customer validation, not SaaS metrics, and building a "category defining" mission that attracted Palantir and Darktrace veterans. His strategy was to operate in stealth until the product was robust, a lesson learned from scaling his previous company, CoinShares, to a $1.2B IPO without traditional venture capital.
After co-founding cybersecurity unicorn NoName Security, which sold to Akamai for nearly $500M, Shay Levi left to start again. He shares the inside story of raising $50M for his new venture, Unframe AI, after getting 19 'no's' from VCs who called his 'try-before-you-buy' enterprise AI model crazy.
After two of her VCs sold their portfolios, Melinda Nicci was left with new, unaligned investors who vetoed a strategic AI spin-out. She shares the negotiation tactics used to buy back 30% of her company, turning a £1M demand into a manageable buyout and reclaiming full control of her profitable business.
After three decades in venture capital, Jon Staenberg of Agate Hound Fund now focuses on search funds, an asset class that acquires profitable, non-sexy businesses and has historically generated 35% net annual returns. He explains the playbook for buying companies at 4-5x EBITDA and why this model offers a more certain path to an exit than traditional VC.
Ben Chiang, who scaled Uber China to 50 million weekly rides, sold his AI startup Forma to Snap for over $100M in just 3.5 years. He reveals how having 18 months of runway gave him the leverage to repeatedly turn down Snap's offers until the price was right, closing the deal just six months before the market turned.
Jenniffer Henderson, founder of HR tech startup Tilt, reveals the brutal reality of raising a Series B in a tough market, a process she calls “100 nos for every one yes.” She shares the harrowing story of a lead investor pulling out after a 3-month exclusivity period and how a subsequent diligence process uncovered a modeling error that cut her valuation by $15M.
With eight exits and over $200M in M&A transactions, Travis Steffen argues that customer retention is 10x more important than acquisition for increasing valuation. He explains how ignoring churn creates a mathematical "carrying capacity" that silently kills growth, a lesson he learned firsthand when VCs rejected his fundraise due to poor retention.
After an 8-figure exit to private equity, John Rood discovered the hardest part of selling a company isn't the deal, but what comes after. He shares how early conversations with PE firms shaped his strategy and why most founders are dangerously unprepared for the loss of identity post-exit.
After a $2.7M fundraise, Shoott.com founder Jennifer Tsai faced a 10x increase in customer acquisition costs post-iOS 14.5, forcing a pivot from VC-style growth to disciplined bootstrapping. By mastering unit economics and data-driven marketing, she scaled the photography marketplace to $10.2M in revenue and nearly $1M in profit, demonstrating how operational rigor can create a valuable, self-sustaining business.
David Connors raised $8M for The Swarm by weaponizing his network, starting with a manual Airtable for his $2M pre-seed and evolving into a data-first API that 10x'd revenue and attracted HubSpot Ventures. His process for mapping warm intros is a masterclass in fundraising leverage and strategic pivots.
Global Objects founder Jess Loren secured her seed round from a single investor by aligning with his mission to digitize the Vatican and holding him to a handshake deal. After turning down a $20M LOI that didn't feel right, she now uses AI to systematically target 260+ VCs for her next $25M round, proving the power of unconventional strategy and gut instinct.
Founders often misuse advisors, giving away a fortune in equity for little more than a name on a slide. Barry Stamos, a 3x exited founder, argues for treating your advisory board like a management team with clear roles, performance-based compensation, and hands-on execution to drive real value—a strategy he used as a founding advisor to help bootstrap Tuft & Needle to $250M in ARR.
While the 2025 IPO market awaits major tech listings to open up, expert Peter Goldstein argues that a small-cap IPO is a viable alternative to VC for founders with 30%+ YoY growth. He details how going public can eliminate VC preference stacks, provide founder control, and create a powerful currency for M&A roll-up strategies.
ZenBusiness founder JC Glancy reveals how he overcame $50k in credit card debt by recruiting HomeAway's founding CTO as CEO, a move that immediately unlocked fundraising and led to a $1B valuation. His story proves why forgoing the "King" title can be the fastest path to getting rich, turning a desperate situation into a unicorn outcome.
Structuring influencer deals isn't about vanity metrics; it's a strategic tool to drive tangible outcomes like lower customer acquisition costs and major retail distribution. Gil Eyal of Stardust Ventures explains how the right equity-for-endorsement deal can lead to a 10-15x valuation jump, while the wrong terms can "choke the company to death."
Four-time founder Adam Spector argues the single biggest mistake early-stage founders make is confusing frugality with focus, wasting precious time on non-core operations. He explains why the moment you take venture capital, you must shift from a cash-scarcity to a time-scarcity mindset or risk failure.
Katelyn Donnelly, a solo GP who bootstrapped and sold her own company to private equity, explains her 'Avalanche' thesis for identifying inevitable market shifts before they become obvious. She reveals why fundraising is a 'matching, not convincing' process and shares the exact red flags—like emails over 250 words—that get a founder's cold email instantly deleted.
Pre-seed investor Dave Lambert explains why his firm, Right Side Capital, sticks to sub-$4M valuations for its 2,000+ investments, arguing that high-valuation rounds often force founders onto a "unicorn or bust" path and eliminate viable $100M exits. He details how capital efficiency and low cash burn create the optionality needed to survive and pivot.
Jeremy Parker, founder of Swag.com, reveals how he navigated an unsolicited acquisition offer from Custom Ink, turning a potential COVID-era crisis into a multi-million dollar exit. He breaks down the negotiation tactics used to command a premium multiple by proving his company’s 100%+ growth rate and superior cash flow model made traditional industry comps irrelevant.
Integrating AI isn't just for tech startups; it's a critical strategy for any founder looking to boost margins and valuation. Jon Tucker explains how he cut a 40-hour, multi-day onboarding process down to 90 minutes at his 200-person agency, HelpFlow, using a framework of "algorithmic thinking" and "Evals" to measure AI performance.
Your startup's revenue and growth rate place you into one of four distinct 'Fundraising Quadrants,' which determines your realistic capital options—from venture capital to private equity, debt, or an acquihire. This framework, explained by host Jason Kirby, helps founders identify their position and stop wasting time pursuing capital partners who aren't a fit.
After bootstrapping his marketplace Bits for Digits to profitability, Laurits Just faced a classic founder crossroads: grind it out, take misaligned VC money, or sell. He chose a strategic exit to Flippa and is now building Flippa Invest, a platform designed to give founders a fourth option—growth capital from investors who actually support a sub-$100M exit.
Rebel Energy founder Penelope Hope explains how she scaled a UK energy supplier to over £100M in revenue with just £1.5M in funding from angels and a crowdfunding campaign. She details the capital-efficient strategy of using robotic process automation to achieve profitability in every month of trading, a rarity in the utilities sector.
David Goldberg, founder of Founders Pledge, explains how he built a system for founders to commit a percentage of their future exit proceeds to charity. He shares the tactical playbook behind deploying over $1.3B with data-driven rigor and launching a $53M venture fund where 85% of the GP carry funds the non-profit's operations.
Likeable Media founder Carrie Kerpen shares the playbook she used to engineer an eight-figure exit, turning her agency into a sellable asset years before the transaction. She details her “RED” revenue framework (Recurring, Expected, Diversified) and the strategic decision to sell at peak market in 2021, a process that went from advisor engagement to close in just four months.
Conor Tomkies bootstrapped his BPO company, Support Ninja, to a mid-eight-figure exit by running the M&A process like a marketing funnel, interviewing 35 bankers, and managing the deal himself to control legal costs. He reveals the tactical playbook he used to navigate a co-founder exit and now applies those lessons as a buyer, acquiring profitable SaaS companies for his holding company, Operator Equity.
David Hauser contrasts bootstrapping Grasshopper to a $175M exit with raising over $75M for Vanilla, revealing why his bootstrapped outcome was 10x larger than his VC-backed competitor's and when to raise capital to dominate an enterprise market. This is a masterclass in choosing the right capital path for the right company.
Patrick Butler built and sold his first major company, Talent Inc., by rejecting the traditional VC path, instead using parent-company-backed debt and a targeted M&A strategy to fuel growth before a successful exit to private equity. This episode details his playbook for using alternative capital to build a valuable, sellable business without relying on venture funding.
The type and cost of debt a startup can access depends entirely on its revenue scale, profitability, and investor backing. Kyle Rector of Boundless reveals that a bootstrapped company might pay 20% interest while a venture-backed peer secures capital for 13%, and a profitable SaaS business could get rates as low as 8%.
DigsConnect founder Alexandria Procter explains how she raised 12M Rand when asking for only 2M, turning a weekend project into Africa's largest student housing platform. She breaks down the massive talent arbitrage in South Africa, where founders can hire experienced, English-speaking engineers for just $3-4k per month.
Patrice King-Brickman of Inspire Access reveals a novel strategy for funding underrepresented founders by legally investing philanthropic capital from Donor-Advised Funds (DAFs) into for-profit startups. This model unlocks a portion of the $240B+ in 'complacent capital' sitting in DAFs, creating a recyclable, tax-advantaged alternative to traditional venture funding.
Most founders are trained to go big or go home, but 90% of startups fail, making the shutdown process a critical, yet overlooked, founder skill. Simple Closure CEO Dori Yona explains how a graceful, well-planned wind-down can preserve investor relationships for your next venture and protect you from years of personal liability and state fines.
Interplay's Mark Peter Davis argues that most companies should not raise venture capital, a lesson from a 13-year career investing in breakout hits like Coinbase and Warby Parker while also bootstrapping 11 companies to successful outcomes. He explains the critical importance of capital strategy alignment, because choosing the wrong path can kill your return as a founder even if the business succeeds.
Nick Telson-Sillett details two distinct capital strategies: bootstrapping his first SaaS company to a $30M exit by reverse-engineering the target number, and then raising a $6M seed round for his next venture by creating 'traction without traction' to build investor FOMO.
Successful fundraising isn't a 90-day sprint; it's a 12-month marathon of strategic relationship building that starts long before you need capital. The process culminates in a month-long meeting blitz, where securing 30 meetings with relevant investors is the key metric that typically leads to one to three term sheets.
After a major bank pulled its $10M Series A term sheet with three weeks of runway left, Arcus founder Edrizio De La Cruz refused to quit, flying to Mexico during an earthquake to save the deal. This resilience defined a journey from four pivots and near-failure to a strategic acquisition by Mastercard after raising over $25 million.
Your goal on a first investor call isn't to get a check; it's to get a second meeting booked before you hang up. With four exits and $135M in transactions, host Jason Kirby explains that founders who control the process—from pre-call research to asking 'Why did you take this call?'—are the ones who successfully earn more of an investor's time.
SAFE agreements, while fast and cheap, can create a financing 'dead zone' where stacked SAFEs convert with massive buying power, leading to devastating founder dilution. Massive VC's Ari Newman argues that paying for a priced seed round early establishes crucial governance and a clean cap table, preventing founders from selling 80% of their company in a single, messy round.
Top Shelf Ventures GP Noah Friedman explains why the multi-trillion-dollar alcohol industry is a massive, underserved market for venture capital, driven by recession-proof demand and tech-like acquisition multiples. He shares his quantitative-first investment criteria focused on velocity and retention, which signal the customer love required to build a brand worth acquiring for nine figures.
Plutoshift founder Prateek Joshi details his journey raising over $16M as a solo founder, sharing the exact enterprise SaaS metrics that unlocked his Series A. Now a VC, he explains why AI should be a 'nitro boost, not the engine' and how founders can manufacture fundraising leverage even with zero network.
Oros Labs CEO Michael Markesbery turned a personal frustration with bulky jackets into a materials science empire by commercializing NASA's brittle aerogel insulation, raising over $50 million. He shares the "super surgical" fundraising process that secured a $22M Series B from strategic investors like Airbus Ventures, detailing how it took 12 months and over a dozen meetings to close the deal in a tough 2023 market.
Deal structure is more important than the headline price, as an aggressive earnout can create leverage for either the buyer or the seller. David Rodnitzky sold his agency for $65M, but when the buyer couldn't pay the earnout, he used his leverage to buy the company back for 65 cents on the dollar before selling it again.
Wyndly founder Aakash Shah explains why he shifted from treating venture capital as a lifeline to treating it as just one option, detailing how he raised capital directly from customers by introducing annual plans—a move that fundamentally changed his company's trajectory.
Serial founder Dan Reich turned a VC rejection into a $725M exit by treating the "no" as a roadmap and ultimately choosing a strategic merger over the funding. His journey building four different companies reveals a masterclass in matching capital strategy to the business model, from bootstrapping and PE-backed CPG to venture-backed deep tech.
After selling Cleversafe to IBM for over $1B, serial entrepreneur Chris Gladwin reveals his playbook for raising capital in tough markets, explaining why he pitched over 300 investors for one round and how he’s avoided down rounds by refusing “crazy” valuations.
Alex Pattis of Riverside Ventures shares the tactical playbook for raising from syndicates, which he used to deploy $75M across 300+ deals. Founders should approach syndicates *after* securing a lead investor, as their success depends heavily on the social proof of who else is in the round.
Wen-Wen Lam sold her $100M top-line startup, Next Travel, after COVID decimated revenue from $10M per month to zero. She reveals the disciplined M&A process for a distressed asset, including the psychological shift required to find opportunity in a crisis and the roll-up pitch that quadrupled her acquirer's valuation.
After a franchise bankruptcy in his 20s, Rob Hunter built a SaaS company to $1M+ ARR, failed to raise a Series A, and still engineered a life-changing 'low eight-figure' exit to a search fund, proving that viable outcomes exist far beyond the traditional VC path.
Ex-M&A lawyer Colby McKenzie raised ~$12M for his cannabis-tech startup, Enlighten, by building with the exit in mind from day one. He reveals how he ran his own bespoke M&A process, creating custom narratives for each potential strategic buyer to secure a successful acquisition by Weedmaps within his 5-year target.
Raising a venture capital fund is often harder than raising for a startup, as emerging managers must sell an intangible product with a 10-year feedback loop. Winter Mead of Coolwater Capital explains why the most fundable GPs in today's market have authentic operator backgrounds, deep sales skills, and a focus on zeitgeist themes like AI and climate.
Solo founder Diana Heldfond raised over $28 million for her edtech startup, Parallel, by strategically starting without a co-founder and "warming up" investors for months before her official raise. Discover her process for turning a $500K pre-seed plan into a full institutional seed round and navigating a Series A with Tiger Global as the market turned.
Going public isn't just for unicorns. IPO expert Peter Goldstein explains the viable path for small and micro-cap companies ($50M-$300M market cap) to access public markets, detailing the real costs, a 12-24 month prep timeline, and the critical mistake of not bringing your own capital to the deal.
After a dot-com bust wiped out his first company, Shane Neman bootstrapped two businesses to successful exits, including an SMS platform he grew to nearly $15M in ARR. Now an active investor, he explains why founders must prove they don't need VC money to attract it and reveals the provocative questions he uses to test their resilience.
Till co-founder Brady Nolan reveals how a single cold LinkedIn message initiated a 5.5-month, founder-led M&A process, resulting in a strategic exit to Best Egg. This case study breaks down the 'bet the farm' decision to kill existing revenue during diligence and why selling was a better capitalization strategy than a Series A.
Sim Desai, founder of secondary market platform Hive, raised $4.25M on a $77M valuation cap to bring transparency to private market liquidity. He explains why the traditional broker-dealer model is broken and how late-stage founders can use structured secondaries to provide liquidity for early employees and investors.
OpenStock provides leverage to LPs in private funds, offering loans against their illiquid positions so they can access cash without selling at a discount. Founder Alex Simpson explains how sophisticated investors use this liquidity to fund everything from tax bills to arbitrage plays, like borrowing at 10% to reinvest in a private credit deal yielding 16%.
After raising $3M for a Web3 stablecoin idea in mid-2022, Bluejay Finance CEO Sherry Jiang navigated two major pivots by meticulously managing burn to extend runway into 2026. She shares her tactical framework for communicating pivots to investors, managing co-founder exits, and maintaining a lean $50k monthly burn to survive market headwinds and find product-market fit.
Proof VC's 'insider access' strategy gives seed funds massive upside by investing their pro-rata rights for them in breakout growth rounds. The model, which splits carried interest 50/50 on a deal-by-deal basis, gives Proof curated access to competitive deals and allows early-stage VCs to participate in wins far beyond their fund's size, as seen in the recent DraftKings acquisition of Jackpocket.
AllStar.gg founder Nick Cuomo turned a $415k pre-seed investment from Mark Cuban into a $12M Series A by navigating the 2021 boom, a crucial seed extension, and a tough 2023 market. He details the metrics, data room strategy, and partnership-led growth that secured the round from Drive Capital.
Ask AI founder Alon Talmor explains how he navigated a fundraising crisis after his prospective COO quit mid-process, ultimately securing a $9M seed and $11M Series A. His core lesson for founders: radical honesty with investors is non-negotiable when a deal is falling apart, as it's the only way to rebuild trust and save the round.
Beehiiv CEO Tyler Denk reveals how he raised over $16M and scaled to $7M ARR by treating traditional fundraising as a "total waste of time." He shares his framework for running hyper-efficient capital raises, including a Series A that went from first call to two term sheets in just six days.
After a four-year grind to $1M ARR with minimal funding, StartLeft Security CEO Jeremy Vaughan raised a $3M seed round by treating fundraising like a sales process and creating investor FOMO. He shares the tactics he used to manage investor relationships, the power of securing a strategic lead, and the satisfaction of turning down VCs who repeatedly moved the goalposts.
Vlada Lotkina, an immigrant founder from Ukraine, raised $12 million for her EdTech startup ClassTag by building her network from scratch and using monthly updates to show progress. She explains why the decision to sell to SchoolStatus was a strategic move and warns founders that most M&A deals fail without a dedicated internal champion at the acquiring company.
Howdy.com co-founder Frank Licea explains how a bootstrapped, profitable service business got into Y Combinator and raised a $3M seed round using a video instead of a pitch deck. He also reveals the near 50/50 equity split he demanded to join as CTO, a critical lesson for founders on how to attract a true technical partner.
First-time founder Kaustav Das raised a $100M debt facility and $10.5M in equity for his fintech, Efficient Capital Labs. He shares his playbook for solving the "chicken and egg" problem between debt and equity investors and reveals the three types of revenue-based financing founders must understand before taking on alternative capital.
After selling her first company, Harvest, to Acorns in 2020, Nami Baral raised $5M in just two weeks for her next venture, Neural, proving an investor's trust is earned over years, not a single pitch. She contrasts the grind of raising $4M as a first-time founder with the momentum-driven, pre-product round she secured as a repeat founder—a masterclass in building leverage.
Summer CEO Paul Kromidas raised $18M in equity and a $50M debt facility by running a structured, multi-threaded process tailored to different capital providers. He hired a former JP Morgan MD to navigate the complexities of the debt facility, a critical move that de-risked the deal and highlights the importance of bringing in experts for high-stakes transactions.
Arch founder Ryan Eisenman raised a $20M Series A after a preemptive offer from client-investors kicked off a compressed, three-week fundraising sprint. This process highlights how a first-time founder can leverage a deeply cultivated, value-driven network to accelerate fundraising and secure capital even when they aren't actively raising.
MicroOne.ai founder Ali Ansari explains how he turned a "staffing agency" into a venture-backable business, raising a $3.3M rolling pre-seed that saw his valuation jump from a $7M to a $30M cap. He reveals the tactical power of productizing services, leveraging founder networks for warm intros, and raising capital on momentum to attract investors like Jason Calacanis.
PR expert Jordan Bantista explains how founders can use media coverage to get on investors' radar *before* a capital raise and why delaying a funding announcement is often a strategic mistake. He provides a tactical playbook for pitching reporters, including the five-sentence rule for getting their attention in a crowded inbox.
Julia Pimsleur, founder of ed-tech company Little Pim, details her journey raising $6 million in venture capital between 2008 and 2014, a time when female founders received less than 2% of funding. She explains how she secured a $1.1M Series A and ultimately engineered a strategic exit to a long-term partner after recognizing she was no longer the right CEO to scale the company.
Zach Bell secured $6M in pre-revenue funding for MyPlace.co by turning a $100K blank check from a friend into a seed round led by Freestyle Capital. His story reveals how a hyper-curated beta and deep investor relationships can overcome the absence of revenue, even in a shifting market.
Foraged founder Jack Hamrick explains how a strategically pitched TechCrunch article in April 2022 turned his bootstrapped marketplace into a hot deal, triggering inbound from over 15 VCs and leading to a $2.7M seed round from Bessemer in just eight weeks. He shares how he filtered investors for mission alignment and strategically delayed the funding announcement for over a year to maximize its impact.
Three-time bootstrapped founder Melissa Kwan explains why avoiding VC enabled her “life-changing” exit for her previous SaaS company, a deal investors would have blocked. She reveals the hidden shareholder risks that almost killed the acquisition and how she now structures capital to reward investors without sacrificing control.
After raising capital every year since 1998 for a total of over $250M, serial entrepreneur Nick Desai explains why fundraising is a constant process and why he once risked his company by rejecting a lowball term sheet to wait six months for a $100M strategic investment from Humana.
Boast AI co-founder Lloyed Lobo shares the playbook for bootstrapping to $10M in revenue by starting as a service business with a zero-person marketing team. He breaks down how this traction led to an unconventional $23M growth equity round that included a significant founder secondary, allowing him to de-risk personally while retaining upside.
How do you raise a $2M seed round for a pre-market medical device? Mustafa Al-Adhami of Aztec Diagnostics combined $1.6M in non-dilutive grants with a clever fundraising tactic: bringing VCs and angels into a hospital for a live product demo that delivered clinical results in minutes, not days.
Bezel founder Quaid Walker raised an $8M seed round by intentionally stacking his cap table with celebrity investors like Kevin Hart, expert operators, and seed-stage VCs. He reveals the tactical decision to delay the public announcement for over a year to weaponize it as a strategic growth lever, not just an ego boost.
Courtyard.io founder Nicolas le Jeune raised $7M pre-revenue by creating massive hype for an NFT drop before it even happened, securing a $3.5M seed round and then another $3.5M immediately after selling out. He shares the playbook for leveraging market timing, a unique partnership with Brinks, and the YC network to drive investor demand in a hot market.
Facing extinction when COVID closed all ski resorts, Unit One used its last $500K to pivot from a niche ski helmet to a high-demand urban mobility product, a move that led to a $3.5M Series A. Co-founder Juan Garcia Mansilla explains how keeping a VC warm with monthly updates for a year resulted in them proactively orchestrating the entire round.
Michael Houck shares the tactical playbook he used to manufacture hype and raise over $15M from investors like a16z for Launch House, using a tiered valuation strategy that 4x’d in just six weeks. He also breaks down how he recovered from a major PR crisis, pivoting to a solo newsletter business that scaled from zero to $50k in monthly revenue in five months.
Mend Labs founder Eziah Zaidi raised a $15M Series A during the peak of the SVB collapse, a process that took four to five months from meeting the lead investor to closing. He reveals how a disciplined, warm-intro-only strategy and radical transparency with investors were critical to navigating market chaos and securing capital from strategic partners like the Walmart family fund.
As a non-technical founder, Sidecar CEO Nik Talreja raised over $16M by strategically sequencing his fundraising, starting with a $1.8M pre-seed on a no-code MVP and culminating in an oversubscribed seed round and a customer-led extension. His playbook demonstrates how deep domain expertise and a customer-driven fundraising process can overcome the lack of an early technical co-founder.
AeroCloud co-founder George Richardson shares the tactical, process-driven system he used to raise a Series A in late 2022, turning a list of 200 target investors into 100 coffee meetings and multiple term sheets in just three and a half months. His framework treats fundraising like a sales funnel, emphasizing preparation, a dedicated team, and a high-volume, condensed outreach process to create momentum and optionality.
After a failed 6-month fundraising process, Wundergraph co-founder Jens Neuse raised a $3M seed round by focusing on "venture-market fit"—a strategy that flips the script and gets VCs to chase you. He explains why cold emails fail and how a single, highly-relevant angel investor from Meta unlocked their entire round.
After raising over $25M for his first company and surviving a painful recap, David Daneshgar chose to bootstrap his second venture, Whippy, to ~$2M ARR by forcing customers to pay upfront—a strategy that gives founders leverage and control that VCs can't ignore.
Brandon Peterson, CEO of Geokey, raised $4.2 million from Nebraska by focusing on an investor's framework of "People, Product, and Profit." He shares how a painful early pitch, where investors ignored his 100-page plan to ask "how are you gonna make money?", taught him to focus on fundamentals and secure a key partnership with Master Lock.
Brett Martin, co-founder of Kumospace, shares the playbook he used to raise $21 million by manufacturing predictable growth to create investor FOMO. He details a tactical fundraising process built on pre-warming target VCs, timing the raise around a key inflection point, and maintaining momentum because, as he learned, 'time kills deals.'
After bootstrapping his first company to a $1.5M exit, former VC Martins Lasmanis shares the tactical playbook for raising a $1.5M+ pre-seed round during a market collapse. He breaks down how his local network delivered his first $410k in one week, and why the next $1M depended entirely on a shift from creative cold outreach to a relentless focus on warm intros.
Trust & Will COO Daniel Goldstein breaks down the tactical fundraising journey to $48M, revealing how pitching over 550 investors and sending relentless monthly updates became their “secret weapon.” This process turned a San Diego startup into a market leader by treating fundraising as a numbers game, not magic.
Romil Verma, co-founder of Outdefine, shares the tactical playbook he and his father used to raise a $2.5M seed round for their Web3 talent platform. He breaks down how they secured lead investors like Jump Crypto after turning down an acquisition offer, navigating 85 VC meetings, and structuring the deal with a SAFE plus token warrant.
Nalu Bio Co-founder Caitlyn Krebs breaks down the year-long, 75+ investor process of raising a $12M Series A for a company that fit neither the biotech nor cannabis mold. She shares how to vet VCs who might not have capital, navigate term sheet negotiations after a prior deal collapsed, and use analogies to pitch a complex business.
Jeff Beck, founder of AnswersNow, raised a competitive Series A at the bottom of the market by timing his fundraise for when he felt "best about the business," not when he hit a specific ARR milestone. He shares his tactical playbook for qualifying investors, managing a 45-day close, and navigating pro rata disputes with early backers.
