SaaS Interviews with CEOs, Startups, Founders

Episode: From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Host: Nathan Latka
Guest: Jared Yaman, CEO of Spresso, Co-Founder of Boxed
Date: February 26, 2026

Episode Overview

In this episode, Nathan Latka interviews Jared Yaman about his entrepreneurial journey from leading Boxed—a direct-to-consumer ecommerce company that raised $380 million and peaked at $187M revenue—to spinning out Spresso, a high-margin SaaS platform now serving global enterprise clients. The discussion candidly explores the growth-at-all-costs era, the hard lessons of heavy dilution, Chapter 11 bankruptcy, and what it takes to pivot from retail operations to SaaS success.

Key Discussion Points & Insights

1. Boxed: Rise and Challenges

• Background & Startup Trajectory

  • Jared’s career began in law, but he pivoted to startups during the 2008 financial crisis.
  • Early ventures in gaming set the stage for Boxed, which launched in 2013, aiming to bring mobile-first experiences to bulk CPG ecommerce.
    • “Let’s go for the big swing, like let’s go for the whole store. And that’s what ecommerce was.” — Jared (03:44)
  • Boxed differentiated itself by centralizing fulfillment and targeting larger basket, rural and B2B consumers.

• Growth, Margins, and Competitive Landscape

  • Boxed’s revenue grew rapidly, reaching $140M in 2018 and $187M by 2020 (per S-1 filings).
  • The company fought “low margin” wars with giants like Amazon, Costco, and Walmart.
    • “Don’t try to compete with Walmart, Amazon and Costco, or if you’re going to do that, you need to put $2 billion on the balance sheet…” — Jared (05:12)
  • Gross profit in 2020 was only $25.9M—around a 4-5% contribution margin.

• Heavy Capital & Founder Dilution

  • Boxed raised $380M in equity. Jared’s founder equity dwindled to ~2.6% by IPO.
    • “When we IPO’d, I was down…to low single digit percent.” — Jared (00:12)
    • “Don’t follow Jared’s model…We took pretty much all of the capital that we brought in and we deployed it for growth and expansion.” — Jared (09:43)
  • He cautions founders about sacrificing personal liquidity and falling into the ‘founders eat last’ trap.
    • “If you don’t take money in the early rounds, you end up really stuck with no way to actually personally get liquidity.” — Nathan (09:09)

• Changing Startup Funding Climate

  • Jared observes a shift away from “growth at all cost” toward capital efficiency and founder-friendly structures.
    • “We’re almost in like peak bootstrap era, right? Capital efficiency, do more with less…” — Jared (08:23)

2. Pivot to Software & Bankruptcy

• Early Signs and Difficult Transition

  • By 2021, retail revenue declined, but software revenue emerged as a “bright star”—$15M contribution in nine months.
  • Pivoting a 9-figure retail business toward SaaS was slow and difficult, requiring stakeholder buy-in.
    • “It is difficult as far as making, turning around the Queen Mary in the harbor.” — Jared (14:19)

• Bankruptcy Process

  • Filed for Chapter 11 on April 2, 2023 after a “slow, slow, slow, then all at once” collapse.
    • “Bankruptcy happens like super, super slow and then all at once. And that’s exactly what I saw.” — Jared (16:04)
  • The collapse of Silicon Valley Bank mid-process exacerbated the cash crunch but wasn’t the sole cause.
    • “It was definitely not SVB’s fault, but we were caught up…just another signal of like, wow, this is an uphill battle…” — Jared (17:42)

3. Spresso: Building a Pureplay SaaS Successor

• Spinning Out & Starting Fresh

  • Key IP, team, and client partnerships (notably, a top 20 global retailer, E.ON) were moved into Spresso.
  • BlackRock, a major debt provider from the Boxed IPO, enabled the spinout and owns a minority stake.
    • “Credit to BlackRock…They facilitated the spinout. We work(ed) with BlackRock very closely on setting up a new cap table, new ownership structure, debt structure…” — Jared (20:46)
  • Spresso had $2.5M ARR at inception (early 2023), maintaining full uptime and service during transition.

• Customer Base & Pricing

  • 15 enterprise customers, with contracts ranging from $20k/year to $2M+/year.
    • “We have customers paying you more than 2 million per year.” — Nathan (21:54)
  • Pricing is modular and tailored—a blend of SaaS modules, implementation fees, and subscriptions, with high-touch discovery/sales.
    • “A lot of SaaS people now feel like they never get their pricing correct…We’ve gone from implementations, also like a modular approach…” — Jared (22:04)

• Revenue Growth and Capital Structure

  • ARR doubled to ~$5M by the end of 2025.
    • “Where you guys finished 2025 in terms of revenue? … Yeah, it’s about double.” — Jared (23:09)
  • Conservative debt: leverage kept at <10% of ARR with 10% interest and under 10% warrants for lenders (mainly BlackRock).
    • “I would say to keep the debt or keep the leverage less than 10% of ARR and then 10% had sort of been our standard interest rate.” — Jared (23:46)
  • Spresso maintained relentless engineering focus—deployment times cut from 4 months to 4 weeks.

• Founder Outlook and Future Plans

  • Jared now prefers capital-efficient growth, but is open to raising more for international expansion.
  • Valuation wisdom: Most SaaS M&A deals happen at 6–7x ARR, not the more “frothy” 10x multiples.
    • “I would say more to ARR, probably more like the 6 or 7 range.” — Jared (26:12)

Notable Quotes & Memorable Moments

• On founder economics:
  • “Don’t follow Jared’s model…We took pretty much all of the capital that we brought in and we deployed it for growth and expansion.” — Jared (09:43)
• On the perils of playing the ‘growth at all costs’ game:
  • “We’re almost in like peak bootstrap era, right? Capital efficiency, do more with less, leverage AI to be maximum efficient…” — Jared (08:23)
• On the Boxed transition to SaaS:
  • “We built some of the best ecommerce software in the world… It’s just more difficult than you would think to pivot that story to a software story.” — Jared (14:19)
• On bankruptcy and SVB:
  • “It was definitely not SVB’s fault, but we were caught up…just another signal of like, wow, this is an uphill battle…” — Jared (17:42)
• On the value of experience over liquidity:
  • “Less about the monetary dollars where possible… I was able to bounce around…leading merchandising, customer service, leading tech teams, leading operations…future earnings as you can stay healthy.” — Jared (11:31)

Timestamps for Key Segments

• [00:00–03:44] Jared’s background, Boxed founding story, early startup experience
• [04:56–06:49] Boxed financials, margin realities, lessons learned in D2C ecommerce
• [09:43–12:38] Founder dilution, equity lessons, advice for modern founders
• [13:48–15:45] The shift toward software, initial SaaS traction inside Boxed
• [16:04–17:42] Chapter 11 bankruptcy, the role of SVB’s collapse
• [18:45–20:34] Spresso spinout mechanics, revenue at spinout, working with BlackRock
• [21:38–22:04] Customer profile, pricing strategy, enterprise SaaS sales motion
• [23:03–24:33] Revenue doubling, conservative debt structure, ARR/valuation math
• [25:10–26:12] Growth, fundraising, view on SaaS multiples and potential exit

Closing Thoughts

Jared Yaman’s story illuminates the highs and lows of ambitious venture-backed startups, the realities of founder dilution, and why sometimes the best software companies are born from hard-earned operational scars. The pivot from “selling detergent” to enterprise SaaS wasn’t quick or easy, but now Spresso stands as a focused, resilient SaaS challenger, serving major enterprise clients—proof that even a bankruptcy can be a new beginning in tech.

Follow Spresso: [SPRESSO AI]
Host/Show: Nathan Latka / SaaS Interviews with CEOs, Startups, Founders