Nov 8, 2021 · 23m · top-founders
FlockFreight Triples Revenue to $300m Last 10 Months, Raises $215m at $1.3b Post
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview with Nathan Latka, Flock Freight founder and CEO Oren Zaslansky explains how the company scaled to a $300 million run rate, raised a $215 million Series D at a $1.3 billion valuation, and automated freight logistics through proprietary pooling algorithms.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 25% of the talking time here. How this is scored →
Nathan as informed peer 5.5 Guest teaching 5.5 Guest disagreement 2.8 Nathan pushing back 4.5
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 7:45 Zaslansky rejects SoftBank markup narrative
Zaslansky openly dismisses Latka's suggestion that SoftBank merely inflated its own valuation, highlighting the $100M brought in by major independent investors like Susquehanna.
Hardest push from Nathan ▶ 17:22 Latka refuses evasive answer on founder equityLatka rejects Zaslansky's generic response about owning a small piece of something big, pressing him repeatedly until he gets a specific bracket on his ownership percentage.
Biggest teaching moment ▶ 18:21 Zaslansky lectures on share preservation and dilutionZaslansky walks Latka and the audience through an operational lesson on why tracking equity percentage instead of share price growth makes founders needlessly anxious.
Nathan holds their own ▶ 13:05 Latka cites historical bill counts to test claimLatka interrupts Zaslansky by referencing exact freight volume figures from their previous interview to stress-test his automation claims.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| The Shared Truckload Algorithm and Revenue Breakdown | 5 | 6 | 2 | 3 | Latka asks Zaslansky to explain how shared truckloads work for non-freight listeners and clarifies run-rate calculations. Zaslansky explains the mechanics of hub-and-spoke vs pooled freight, correcting Latka's assumption that guarantees only matter on the driver supply side. | |
| Gross Margins, Supply Automation, and the $215M Series D | 6 | 6 | 4 | 5 | Latka presses Zaslansky on whether Flock Freight has true SaaS gross margins and jokes that SoftBank is simply marking up its own portfolio. Zaslansky pushes back, breaking down why their COGS remain significant on the supply side and detailing the syndicate of new outside investors in the Series D. | |
| Sponsor Message: Flatfile Data Onboarding Platform | 5 | 4 | 2 | 4 | Following a sponsor read, Latka points out that a $1.3B valuation on a $300M run rate represents a compressed multiple compared to typical tech startups. Zaslansky agrees and contextualizes Flock Freight within an Amazon-style COGS framework rather than a pure Google-style software model. | |
| Operational Metrics, Supply Automation Targets, and M&A Strategy | 6 | 5 | 3 | 5 | Latka interrupts to challenge Zaslansky with historical bill volumes cited during their previous interview. Zaslansky clarifies the difference between total freight bills and the percentage of transactions moving through end-to-end supply automation. | |
| Purpose-Driven Entrepreneurship, B-Corp Status, and Employee Liquidity | 6 | 7 | 4 | 7 | Latka repeatedly probes Zaslansky to disclose his exact equity ownership percentage. While initially deflecting, Zaslansky provides an in-depth lesson on share count preservation, dilution philosophy, and early-stage tax considerations before confirming he remains in double digits. | |
| Putting Venture Capitalists to Work: Pre-IPO Readiness and Hiring | 5 | 5 | 2 | 3 | Latka asks how a founder effectively extracts work from high-profile mega-investors like SoftBank. Zaslansky outlines his strategy of using VC board members for pre-IPO readiness and executive talent sourcing. |
Statements from this episode (17)
Flock Freight unlocked product-market fit via shared truckload guarantees in 2019
“And we figured that out in early 2019. And that was a guarantee of a shared truckload at the point of purchase.”
Flock Freight grew revenue from $25M to $100M in 2020
“We go from twenty five million to a hundred million by the end of the year.”
Flock Freight expects $330M-$340M run rate in October 2021
“We will do more than twenty five million in the month of October. So our run rate will be, you know, three thirty, three hundred forty million you know give or take in the month of October.”
Flock Freight raised $215M from SoftBank at a $1.3B valuation
“We raised two hundred and fifteen million dollars led by a soft bank vision fund too. They led our last round as well. This was a real preemption, you know, with these numbers, they came to us mid year, six months into the last round. And said, you know, giddy…”
SoftBank offered up to $300M before Flock Freight reduced the check size
“SoftBank was about half of the check in this round. You know, we had another hundred million dollars come in on top of what SoftBank wrote. SoftBank wanted to write a much larger check, initially up to three hundred million. And from around construction standp…”
Flock Freight offered secondary liquidity to early employees, but not investors
“A little bit of liquidity to early folks, but only, only team members, not, not investors. No investors want it out. I can certainly say that.”
Flock Freight moved roughly 16,000 freight bills in September 2021
“I mean, we moved last month now already like 16,000 freight bills in the month.”
Flock Freight aims to automate 80% of supply transactions within 18 months
“It's only about 10% of the transactions on that end are really totally automated at this point. We want to take that number up. It's not going to be a hundred percent, but to 80 or 90%, and we want to do that in the next 12 to 18 months.”
Flock Freight is the only certified B Corp in the freight industry
“We're the only certified B Corp in freight.”
Flock Freight claims it can cut greenhouse gas emissions by 40%
“We have an opportunity to make a 40% reduction in greenhouse gas if we're successful at scale.”
Flock Freight's Series A post-money valuation was roughly $58M
“That was 57 or eight. It was no post. The pre was like 41, 42, you know, something along those lines.”
Flock Freight plans to reach 800 employees by late 2022
“We're going to be seven, 800 by this time next year.”
Oren Zaslansky retains double-digit equity at Series D but expects dilution
“I am not yet in the single digits. I will.”
SoftBank founders interact primarily with deal teams, not Masayoshi Son
“Working with Masa is a tiny piece of what we do when you're a SoftBank portfolio company, but really you live within your deal team.”
Flock Freight raised nine financing rounds without a single down round
“We've raised nine rounds about half price kind of series C through series D and also some notes in between, you know, cause you're getting started or bridges, up bridges, never down bridges, but kind of the good bridges and the hard bridges along the way.”
Flock Freight is preparing for an IPO in two to three years
“This business is headed to the public markets. We're not yet ready to hire a banker. We're not yet ready to start talking to the exchanges. So it's, I wouldn't quite call us pre-IPO, but we're pre-pre-IPO, meaning find me people that can educate me on the stor…”