From $187M Ecommerce to $5M ARR SaaS: Spresso’s Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Release Date: 02/26/2026
This Ugly Website Does $106M/Year (866,000 Pay For It)
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Vadim Yasinovsky, co-founder of pdfFiller and CEO of airSlate (parent of pdfFiller, signNow, DocHub, US Legal Forms, airSlate Flow), breaks down how a plain-looking PDF editor page became a $106M/year product with 866,000 paying customers — inside a company doing $200M in revenue across 1.1 million customers at an average of $180/year. He raised just $150M total (last round: $52M at a $1.25B valuation in June 2022) and now says the company is optimistically worth $800M — despite doubling revenue since. He bought signNow at $3M and grew it to $35M. He built an SEO machine on 4.8 billion...
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"I Built My Own AI Video Model, Now Make $3M a Month," Akool CEO Jeff Lu
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Jeff Lu quit Google Cloud in 2022 to build his own AI video models at Akool, a generative AI platform for avatars, face swap, and video translation. He skipped the giant foundation models and trained small ones for specific tasks on rented servers, then watched revenue go from $100K in 2022 to $3M in 2023, $13M in 2024, $25M in 2025, and over $3M in June 2026 alone. He breaks down why Coca-Cola picked him over the foundation models and now pays him $4m per year. He'll share how he's driven huge usage (500,000 images and videos created daily) and what he'd say if Google offered $500M cash....
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You Make $8m/yr, Would You Sell for $100m Cash? | Antoine Fort, CEO Qobra
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Antoine Fort launched Qobra in 2020 with a $100K pre-seed from 7 angels, and his first investor was also his first customer. He started by cold calling with a phone list from a provider later shut down over European privacy law (GDPR), charging $10K/year. Today Qobra is at about $30K/year per customer, 250+ customers, and roughly $7–8M ARR. Along the way, one meme ad closed an $80K/year deal, and a single sales rep on the platform earned $1.5M in commissions (75x the average). So when Nathan asks if he'd sell for $100M cash today, his answer is surprisingly honest. Qobra is an AI-first sales...
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How He Makes $40M/yr Renting Laptops for $50/Mo | Sevan Marian, CEO Fleet
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Sevan Marian, co-founder and CEO of Fleet, bootstrapped his Paris-based laptop rental company for 7 straight years to roughly $40M in annualized revenue and close to $10M in yearly profit (EBITDA), without raising a single dollar of VC. His trick: customers pay about $50/month on 36-month contracts, and Fleet sells each contract to a bank that pays it upfront on day one. That's how he's financed 50,000+ devices across 20 countries without holding inventory. In early 2026 he sold about 25% of the company at a $100M valuation, and every dollar went out to the team: employees cashed out 100% of...
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How Does Laundry Software Make $60M a Year? | Alex Jekowsky CEO TryCents
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At 23, Alex Jekowsky started building Cents, an all-in-one software, hardware, and payments platform for laundromats, dry cleaners, and shared laundry rooms. In 2025, Cents generated $60 million in revenue, up 67%, with just 80 employees and EBITDA margins above 20%. The company now has 99% customer retention, powers laundry rooms in nearly 7,000 apartment buildings, and recently raised a $140 million Series C at an approximately $800 million valuation. In this episode, Alex reveals: • How Cents grew from $700,000 to $60 million in four years • Why its first customer was a 73-location...
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FrodaEmbedded.com hits $80m Revenue by Lending to 150k SMB's | CEO Oliver Mohseni
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Froda generated $57 million in revenue in 2025 by lending to the small businesses traditional banks often overlook. In this episode, Nathan Latka sits down with Froda co-founder Oliver Mohseni to unpack the economics behind the startup bank. Froda has supported 150,000 businesses across seven markets and funded approximately $3.45 billion since launch. Oliver explains how Froda uses retail deposits, automated underwriting, and embedded partnerships with banks, fintech companies, payment providers, and software platforms to scale its lending operation. Listen to learn: • How Froda makes money...
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He Makes $50m/yr on Cookie Popups, Controls 2% of all Web Traffic
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Raphaël Boukris is the co-founder and Chief Revenue Officer of Didomi (didomi.io), the Paris-based consent management platform that helps enterprises comply with GDPR, CCPA, and privacy laws worldwide. Roughly 2% of all global web traffic passes through Didomi's SDK, and the company processes billions of consent decisions every month for customers including Bloomberg, Sky, and Adyen. In this interview, Raphaël breaks down the full financial history on the record: three funding rounds, two acquisitions, and a majority sale to private equity. He raised under €300k from angels, then €5m...
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Why Does Google Pay Him $2M A Year?
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Stéphane Donzé has bootstrapped AODocs and Talarian to a combined $60m in 2026 revenue without raising capital. His top three customers each pay more than $2m per year, including Google, which pays him millions annually to control the documents behind its data center builds. He funded fourteen years of R&D off a cloud consulting business, never burned more than $200k in a month, and has fielded private equity calls four times a week declining $600m offers.
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How He Bootstrapped Dental Software to $16m
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He bootstrapped to $16.5m ARR selling software to 2,000 dental offices. Zero dollars raised, 24% EBITDA, and $1.5m in free cash flow last year. COVID cut him back to $2m in 2021; he's added $14.5m since, charging $13k per dental office per year. When I asked what happens if Henry Schein shows up with $180m cash, he gave a surprising answer.
info_outlineHow do you turn a failed public ecommerce company into a $5M ARR enterprise SaaS platform serving ~$2M+ contracts — while rebuilding with capital efficiency after bankruptcy and avoiding the growth-at-all-costs playbook?
In this episode, Nathan sits down with Jared Yaman, co-founder of Spresso and former founder of Boxed, the bulk ecommerce company that scaled to $187M in revenue before its IPO and eventual Chapter 11 restructuring. Today, Jared leads Spresso, the enterprise ecommerce software platform spun out of Boxed, now serving roughly 15 enterprise customers worldwide and growing ARR from $2.5M at spinout in 2023 to about $5M in 2025 through large ACV enterprise contracts.
What makes this story interesting is the transition from low-margin ecommerce operations to high-margin enterprise SaaS. Boxed generated hundreds of millions in revenue but operated on ~4–5% contribution margins. Spresso keeps the infrastructure, data, and enterprise relationships — but monetizes them through implementation fees and modular SaaS subscriptions, fundamentally changing the economics.
You’ll learn:
- Why scaling revenue without contribution margin destroys optionality, even at $100M+ revenue
- How enterprise implementation fees subsidize onboarding costs and accelerate payback periods
- The pricing structure behind $2M+ enterprise contracts in ecommerce infrastructure
- Why founder-led sales and existing network relationships became the primary GTM channel post-spinout
- How to reposition operational technology into a standalone SaaS category buyers understand
- The debt strategy Spresso uses to keep leverage under 10% of ARR
- Lessons from raising $380M in venture capital and ending with low single-digit founder ownership
- How reducing deployment timelines from 4 months to 4 weeks unlocked enterprise expansion
- Why enterprise SaaS growth favors fewer customers with large ACVs over broad SMB distribution
- The strategic shift from retail unit economics to recurring software margins
Jared previously co-founded Boxed, raising roughly $380M before taking the company public, where founder ownership diluted to about 2.6%. After Boxed filed for Chapter 11 in April 2023, he helped spin out the software platform into Spresso with debt financing support, rebuilding the business around sustainable SaaS economics instead of venture-funded retail growth.
This episode is for founders navigating pivots, operators moving from services or commerce into SaaS, and investors studying capital efficiency in enterprise software. It’s a masterclass in restructuring strategy, enterprise pricing, and rebuilding a company around durable margins instead of headline revenue.
Watch this episode on YouTube: https://youtu.be/vslJtgAtjuY
Connect with Jared: https://www.spresso.ai/
Connect with Nathan: FounderPath.com