Nov 8, 2018 · 23m · top-founders
1202 He Raised $20m+ in First Company, Now Bootstrapping in B2B Sales Tech Space, $1m in ARR
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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 episode of The Top Entrepreneurs, host Nathan Latka interviews Adam Schoenfeld, who shares how he transitioned from raising over $20 million at Simply Measured to bootstrapping B2B sales automation platform Siftrock to $1 million in ARR with a team of six.
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 42.3% of the talking time here. How this is scored →
Nathan as informed peer 4.1 Guest teaching 2.1 Guest disagreement 0.8 Nathan pushing back 2.0
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:31 Rejecting LTV calculations in early-stage SaaS
Adam pushes back on Nathan's attempt to calculate LTV, stating that computing lifetime value on early cohorts with low churn leads to nonsensical projections.
Hardest push from Nathan ▶ 10:14 Pressing on cap table equity splitNathan directly challenges Adam on whether he is a genuine co-founder with meaningful equity rather than an advisor with a single-digit stake.
Biggest teaching moment ▶ 16:31 Adam explains why early cohort LTV is misleadingAdam educates Nathan on why focusing on CAC payback and renewal rate is far more practical than projecting multi-decade LTV on early customer cohorts.
Nathan holds their own ▶ 17:35 Nathan drills into gross vs net retentionNathan immediately catches the nuance in Adam's renewal stats, clarifying the distinction between 99.5% gross retention and 135% net retention.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Adam Schoenfeld's Background and Simply Measured Exit | 5 | 4 | 1 | 2 | Nathan inquires about Simply Measured's exit and fundraising history, sharing his own background in social analytics. Adam clarifies his departure timeline prior to the Sprout Social acquisition while remaining collaborative. | |
| Understanding the Siftrock Value Proposition and Genesis | 4 | 3 | 1 | 3 | Nathan probes into Adam's exact title and whether internal conflict led to his joining Siftrock. Adam clarifies the backstory of teaming up with solo technical founder Chris Hundley. | |
| Pricing Architecture and Crossing the $1M ARR Threshold | 5 | 2 | 0 | 2 | Nathan and Adam analyze Siftrock's pricing tiers and expansion levers. Nathan calculates ARR from customer count and ACV, commending Adam on reaching the $1M ARR milestone on zero capital. | |
| Shifting Mindset from VC Scale to Hands-On Bootstrapping | 4 | 2 | 1 | 3 | Nathan questions Adam on how he adjusted from managing large VC-backed teams to doing hands-on tactical work. He presses on the equity split and cap table, which Adam clarifies represents a true co-founder partnership. | |
| Sponsor Segment: Project Management with Monday.com | 5 | 1 | 0 | 1 | Following a mid-roll sponsor read for Monday.com, Nathan explores Siftrock's growth velocity and initial sales hire economics. Adam breaks down their 18-month path from $100k to $1M ARR and a 6-month CAC payback. | |
| SaaS Retention Metrics and Seattle Team Culture | 6 | 4 | 2 | 3 | Adam dismisses traditional LTV metrics for early-stage SaaS cohorts, arguing CAC payback and renewal rates are far more meaningful. Nathan digs into gross versus net dollar retention metrics and team location. | |
| Strategic Roadmap, Breakeven Execution, and Acquisition Views | 4 | 1 | 1 | 2 | Nathan asks about strategic product goals and tests Adam's willingness to sell for a hypothetical $5M offer. Adam rejects a lowball exit in favor of running a cashflow-positive bootstrapped business before completing the Famous Five. | |
| Nathan Latka's Episode Summary and Conclusion | 0 | 0 | 0 | 0 | Nathan recaps Adam's background, Siftrock's value proposition, customer numbers, ARR milestone, and retention metrics in a concluding outro monologue. |
Statements from this episode (13)
Schoenfeld: Simply Measured reached more than a couple million in ARR
“It was definitely more than a couple, but I can't share details about that.”
Schoenfeld: Bootstrapping is better than venture capital for many businesses
“I'm not, like, violently opposed to the VC model. I just think there's lots of businesses and lots of opportunities to you know, take a different approach, to take a more, a little bit of a slower, kind of more intentional approach to kind of the market, and t…”
Schoenfeld: Siftrock ACV averages $7,500 per year
“Yeah, so on average, existing business, it's 7500 per year.”
Schoenfeld: Siftrock reached $1M ARR bootstrapped with 5 employees
“I mean, a six employee, we just hired our sixth employee. So you know, functionally a five employee company reaching a million of ARR on zero capital.”
Latka: Early-stage interviews get 3x more downloads than pre-IPO founders
“The interviews I do with people that are at your level get almost three times the downloads as when I have Ryan on from Qualtrics and they're about to IPO.”
Schoenfeld: Siftrock cap table gives him true co-founder equity
“No, no, I'm a true co-founder in that sense. I mean, obviously we tilted it a little bit for, you know, him and the sacrifices he's made, but it's a, it would be a typical, you know, if we had started the company and I had to pay for that, right?”
Schoenfeld: Siftrock grew from $100K to $1M ARR in 18 months
“I mean, we went, we, it took us 18 months to go from basically a hundred K to a million of AOR. So, you know, when I came in, we were about a hundred K of just what he'd cobbled together. And, you know, we just crossed the 1,000,018 months after.”
Schoenfeld: Siftrock CAC is half of ACV with six-month payback
“Yeah, so it's about half of what our ACV is. It takes us about six months to pay it back. So call, I mean, it fluctuates, you know, some quarters it's four, some it's eight, right?”
Schoenfeld: Calculating LTV on early SaaS cohorts is completely useless
“I don't think about LTV and SAS. I just look at the CAC ratio and then the, and the payback period. Cause I think when you start doing LTV on a half a percent of churn on an early cohort, it's like your LTV is a hundred years or something.”
Schoenfeld: Siftrock Has 99.5% Gross Dollar Renewal Rate
“If I just look at everybody who's renewed over the last 18 months, we have a 99.5% dollar gross renewal rate”
Schoenfeld: Siftrock would reject a $5 million acquisition offer today
“Not for five. I mean, everybody's got some number, right? I'm not going to share it on your show here, but I think we are building the business as if we're going to be doing this in And if those conversations happen, like we'll, we'll entertain them.”