The Ledger

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why aren't all 17 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Insight
Yaman: The 'founders eat last' mentality is antiquated
“Don't do the move of like founders eat last. I also think that's old and antiquated. Like you have to understand your worth.”
Jared Gaiman Feb 26, 2026 ▶ 10:19 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Insight
Yaman: Competing with Walmart and Amazon requires $2 billion and 10 years
“Don't try to compete with Walmart, Amazon, and Costco. That's, or if you're going to do that, you need to put Two billion dollars on the balance sheet and you need to make that like a 10 year journey.”
Jared Gaiman Feb 26, 2026 ▶ 5:16 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Disclosure
Yaman made under $10M in personal liquidity despite Boxed raising $380M
“Yeah, it was not the case.”
Jared Gaiman Feb 26, 2026 ▶ 11:31 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Opinion
Yaman: Boxed went public via SPAC before it was fundamentally ready
“So we did go public via SPAC. So we were kind of in the public markets, maybe over our skis a little bit, not fully ready to be there, whether that's from a KPI standpoint, growth standpoint, or just fundamentals standpoint.”
Jared Gaiman Feb 26, 2026 ▶ 16:17 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Opinion
Yaman: Boxed's collapse wasn't SVB's fault; would bank with them again
“Pretty impressive how SVB has turned it around. I would bank with them again, timing, you know, a lot of things come down to timing. So it was definitely not SVB's fault, but we were caught up.”
Jared Gaiman Feb 26, 2026 ▶ 18:07 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Insight
Yaman: CPG e-commerce removes merchandising risk compared to apparel
“The beauty of that was we're now not in charge of the merchandising. Like, you know, these, you know what a Cheerio is, you know, if you want it, you know, a Ziploc bag. So we essentially just focused on the fulfillment, laugh-mouth delivery and the customer e…”
Jared Gaiman Feb 26, 2026 ▶ 4:07 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Insight
Yaman: Boxed burned capital targeting idealized rather than actual customers
“I feel like we marketed towards the customer we wanted to be a boxed Customer versus the customer who actually was that creates marketing and efficiency.”
Jared Gaiman Feb 26, 2026 ▶ 12:54 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Assertion Not checkable as stated
Yaman: A top-20 global retailer chose Spresso over Amazon and Rakuten
“We have a retailer, top-twenty retailer in the world. They looked at everything. They looked at using Amazon, Rakuten, local providers, in-house solution, and they chose the espresso solution because they did see that it's a superior software platform”
Jared Gaiman Feb 26, 2026 ▶ 15:23 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Opinion
Yaman: Boxed couldn't beat Walmart on logistics, but could on tech
“We're not going to be able to out supply chain, out trucking, out logistics, out warehouse, you know, Walmart and Kroger and the major retailers in the U S especially with consumables, but we still feel like we can, you know, out technology them.”
Jared Gaiman Feb 26, 2026 ▶ 16:38 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Assertion Supported
Yaman: BlackRock held Boxed debt and facilitated the Spresso spinout
“So BlackRock had put in a debt instrument into the IPO process. BlackRock believed in the team. They believe the technology, the relationships that we have built. So working with our number one customer, right? We had to make sure they were on board. That's Eo…”
Jared Gaiman Feb 26, 2026 ▶ 21:02 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Opinion
Yaman: Realistic enterprise SaaS valuation multiples are currently 6x to 7x ARR
“I would probably caution people that in our business, a certain type of business, the multiple is probably more in the six or seven range.”
Jared Gaiman Feb 26, 2026 ▶ 26:56 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Assertion Not checkable as stated
Yaman: Boxed had exactly one profitable month during its entire history
“We did have a profitable month.”
Jared Gaiman Feb 26, 2026 ▶ 5:50 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Assertion Not checkable as stated
Yaman: Boxed peaked at a 4% to 5% contribution margin
“If we were to hit a four to five percent contribution margin, that was a big win. And that was pushed by every, every lever we could possibly pull from vendor marketing.”
Jared Gaiman Feb 26, 2026 ▶ 5:56 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Disclosure
Yaman: Held low single-digit equity percentage at Boxed IPO
“When I, when we IPO'd, I was down as a startup or as a founder to single digit percents, low, low percent, single digit percentage”
Jared Gaiman Feb 26, 2026 ▶ 8:02 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Disclosure
Yaman: Spresso serves 15 customers ranging from $20K to millions in ARR
“About 15. But that's from say 20,000 ARR to X amount of millions of ARR.”
Jared Gaiman Feb 26, 2026 ▶ 21:41 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Disclosure
Yaman: Spresso doubled its ARR from $2.5M to $5M by 2025
“Yeah, it's about double.”
Jared Gaiman Feb 26, 2026 ▶ 23:10 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Disclosure
Yaman: BlackRock restricts Spresso's venture debt to under 10% of ARR
“You know, basic target would say to keep the debt or keep the leverage less than 10% of ARR, and then 10% has sort of been our standard interest rate, and that's something that actually sort of came from BlackRock.”
Jared Gaiman Feb 26, 2026 ▶ 23:55 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
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