From $187M Ecommerce to $5M ARR SaaS: Spresso’s Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Release Date: 02/26/2026
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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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The Surprising Way This Startup Bank Makes Millions
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Featherless: $3.6M Revenue Running 6,700 Open Source AI Models — Eugene Cheah
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How do you go from a pricing experiment inside a failing product to $3.6 million in annual revenue with 10,000 customers — in under two years and with zero paid marketing? Eugene Cheah is the co-founder and CEO of Featherless.ai, the largest open source LLM inference provider on Hugging Face. He co-created RWKV, the first attention-free AI architecture under the Linux Foundation, and today runs a 27-person team serving customers that pay anywhere from $25 a month to $2 million a year. You'll learn: Why Featherless started as an accident — a pricing experiment that outperformed the...
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