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Jul 28, 2022 · 18m · top-founders

He just hit $12m in ARR. Took 7 years to hit $1m. Don't get discouraged!

Daniel Wickberg · 10m spoken Nathan Latka · 5m spoken
0:00 / 0:00

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, UpSales founder and CEO Daniel Wickberg discusses his 20-year journey from bootstrapping and taking seven years to hit $1 million ARR to scaling a publicly traded SaaS CRM generating $13 million ARR with strong profitability.

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 35.3% of the talking time here. How this is scored →

Nathan as informed peer 5.2 Guest teaching 1.4 Guest disagreement 0.8 Nathan pushing back 2.2
05100:0010:000:45–4:13 · Nathan as informed peer 6/10 Introducing UpSales CRM and Product Positioning Latka demonstrates immediate familiarity with SaaS metrics and compares the product positioning directly to tools like SaaSOptics and Baremetrics. Wickberg clarifies how a white-label partner migration temporarily distorted their average contract value.4:13–9:25 · Nathan as informed peer 6/10 The Early Slog: Bootstrapping and Reaching One Million Latka presses into the 7-year timeline to reach one million ARR and meticulously dissects the mechanics of Wickberg's pre-IPO secondary sale and partner buyout. Wickberg clarifies that both parties sold secondary equity simultaneously rather than an internal direct cash buyout.9:28–11:49 · Nathan as informed peer 4/10 Founderpath Valuation Tool Advertisement Following a sponsor ad read, Latka explores why the company chose an IPO on Sweden's First North exchange over private equity, with Wickberg detailing their desire for operational autonomy.11:49–16:02 · Nathan as informed peer 7/10 Net Retention Targets and Churn Reduction Focus Latka runs quick mental calculations on net retention, monthly free cash flow generation of 250k dollars, and Rule of 40 benchmarks. Wickberg manages public company disclosure limitations around gross churn while sharing expansion and retention targets.16:03–18:00 · Nathan as informed peer 3/10 Famous Five: Executive Tools and Business Advice A swift, cordial Famous Five concluding sequence where Latka pauses briefly to ask how the guest uses an automated LinkedIn outreach tool before wrapping up with a recap.0:45–4:13 · Guest teaching 2/10 Introducing UpSales CRM and Product Positioning Latka demonstrates immediate familiarity with SaaS metrics and compares the product positioning directly to tools like SaaSOptics and Baremetrics. Wickberg clarifies how a white-label partner migration temporarily distorted their average contract value.4:13–9:25 · Guest teaching 2/10 The Early Slog: Bootstrapping and Reaching One Million Latka presses into the 7-year timeline to reach one million ARR and meticulously dissects the mechanics of Wickberg's pre-IPO secondary sale and partner buyout. Wickberg clarifies that both parties sold secondary equity simultaneously rather than an internal direct cash buyout.9:28–11:49 · Guest teaching 1/10 Founderpath Valuation Tool Advertisement Following a sponsor ad read, Latka explores why the company chose an IPO on Sweden's First North exchange over private equity, with Wickberg detailing their desire for operational autonomy.11:49–16:02 · Guest teaching 1/10 Net Retention Targets and Churn Reduction Focus Latka runs quick mental calculations on net retention, monthly free cash flow generation of 250k dollars, and Rule of 40 benchmarks. Wickberg manages public company disclosure limitations around gross churn while sharing expansion and retention targets.16:03–18:00 · Guest teaching 1/10 Famous Five: Executive Tools and Business Advice A swift, cordial Famous Five concluding sequence where Latka pauses briefly to ask how the guest uses an automated LinkedIn outreach tool before wrapping up with a recap.0:45–4:13 · Guest disagreement 1/10 Introducing UpSales CRM and Product Positioning Latka demonstrates immediate familiarity with SaaS metrics and compares the product positioning directly to tools like SaaSOptics and Baremetrics. Wickberg clarifies how a white-label partner migration temporarily distorted their average contract value.4:13–9:25 · Guest disagreement 2/10 The Early Slog: Bootstrapping and Reaching One Million Latka presses into the 7-year timeline to reach one million ARR and meticulously dissects the mechanics of Wickberg's pre-IPO secondary sale and partner buyout. Wickberg clarifies that both parties sold secondary equity simultaneously rather than an internal direct cash buyout.9:28–11:49 · Guest disagreement 0/10 Founderpath Valuation Tool Advertisement Following a sponsor ad read, Latka explores why the company chose an IPO on Sweden's First North exchange over private equity, with Wickberg detailing their desire for operational autonomy.11:49–16:02 · Guest disagreement 1/10 Net Retention Targets and Churn Reduction Focus Latka runs quick mental calculations on net retention, monthly free cash flow generation of 250k dollars, and Rule of 40 benchmarks. Wickberg manages public company disclosure limitations around gross churn while sharing expansion and retention targets.16:03–18:00 · Guest disagreement 0/10 Famous Five: Executive Tools and Business Advice A swift, cordial Famous Five concluding sequence where Latka pauses briefly to ask how the guest uses an automated LinkedIn outreach tool before wrapping up with a recap.0:45–4:13 · Nathan pushing back 2/10 Introducing UpSales CRM and Product Positioning Latka demonstrates immediate familiarity with SaaS metrics and compares the product positioning directly to tools like SaaSOptics and Baremetrics. Wickberg clarifies how a white-label partner migration temporarily distorted their average contract value.4:13–9:25 · Nathan pushing back 4/10 The Early Slog: Bootstrapping and Reaching One Million Latka presses into the 7-year timeline to reach one million ARR and meticulously dissects the mechanics of Wickberg's pre-IPO secondary sale and partner buyout. Wickberg clarifies that both parties sold secondary equity simultaneously rather than an internal direct cash buyout.9:28–11:49 · Nathan pushing back 1/10 Founderpath Valuation Tool Advertisement Following a sponsor ad read, Latka explores why the company chose an IPO on Sweden's First North exchange over private equity, with Wickberg detailing their desire for operational autonomy.11:49–16:02 · Nathan pushing back 3/10 Net Retention Targets and Churn Reduction Focus Latka runs quick mental calculations on net retention, monthly free cash flow generation of 250k dollars, and Rule of 40 benchmarks. Wickberg manages public company disclosure limitations around gross churn while sharing expansion and retention targets.16:03–18:00 · Nathan pushing back 1/10 Famous Five: Executive Tools and Business Advice A swift, cordial Famous Five concluding sequence where Latka pauses briefly to ask how the guest uses an automated LinkedIn outreach tool before wrapping up with a recap.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 46.3% · guest 53.7%0:00 · Nathan 46.3% · guest 53.7%3:00 · Nathan 36.2% · guest 63.8%3:00 · Nathan 36.2% · guest 63.8%6:00 · Nathan 20.5% · guest 79.5%6:00 · Nathan 20.5% · guest 79.5%9:00 · Nathan 51.3% · guest 48.7%9:00 · Nathan 51.3% · guest 48.7%12:00 · Nathan 19.1% · guest 80.9%12:00 · Nathan 19.1% · guest 80.9%15:00 · Nathan 27.2% · guest 72.8%15:00 · Nathan 27.2% · guest 72.8%18:00 · Nathan 96.7% · guest 3.3%18:00 · Nathan 96.7% · guest 3.3%
Sharpest disagreement ▶ 12:49 Wickberg declining to disclose gross churn due to public listing

When Latka directly asks for annual gross churn, Wickberg firmly sets a boundary, stating that as a publicly listed firm it is a KPI they do not publicly report.

 Hardest push from Nathan ▶ 7:32 Latka challenging the structure of the pre-IPO secondary round

Latka refuses to let the secondary structure remain vague, repeatedly clarifying whether Wickberg used the five million to buy out his co-founder's eight percent stake.

 Biggest teaching moment ▶ 2:19 Wickberg detailing the ARPU skew from a bulk migration

Wickberg educates Latka on why their average contract values look lower on paper, explaining how tripling their customer count overnight via a partner migration diluted the metric.

 Nathan holds their own ▶ 14:55 Latka calculating free cash flow and Rule of 40 performance

Latka instantly translates Wickberg's thirty-five percent growth and twenty-five percent free cash flow margins into exact bottom line dollar amounts and evaluates their Rule of 40 standing.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing UpSales CRM and Product Positioning 6212 Latka demonstrates immediate familiarity with SaaS metrics and compares the product positioning directly to tools like SaaSOptics and Baremetrics. Wickberg clarifies how a white-label partner migration temporarily distorted their average contract value.
The Early Slog: Bootstrapping and Reaching One Million 6224 Latka presses into the 7-year timeline to reach one million ARR and meticulously dissects the mechanics of Wickberg's pre-IPO secondary sale and partner buyout. Wickberg clarifies that both parties sold secondary equity simultaneously rather than an internal direct cash buyout.
Founderpath Valuation Tool Advertisement 4101 Following a sponsor ad read, Latka explores why the company chose an IPO on Sweden's First North exchange over private equity, with Wickberg detailing their desire for operational autonomy.
Net Retention Targets and Churn Reduction Focus 7113 Latka runs quick mental calculations on net retention, monthly free cash flow generation of 250k dollars, and Rule of 40 benchmarks. Wickberg manages public company disclosure limitations around gross churn while sharing expansion and retention targets.
Famous Five: Executive Tools and Business Advice 3101 A swift, cordial Famous Five concluding sequence where Latka pauses briefly to ask how the guest uses an automated LinkedIn outreach tool before wrapping up with a recap.

Statements from this episode (14)

Disclosure
UpSales Pivoted to Target Recurring Revenue Businesses After Starting as CRM
“We started out as a typical CRM almost 20 years ago. And then we did a pivot a few years ago to start focusing more on, on recurring revenue businesses like ourselves.”
Daniel Wickberg Jul 28, 2022 ▶ 1:11
Opinion
UpSales Built SaaS-Specific KPI Tracking Because Other CRMs Made It Hard
“We do revenue recognition. We do all kinds of ARR and MRR analytics, and we spend quite a lot of time to, you know, enable our customers to manage SAS specific KPIs and targets, which is kind of a hassle in most other CRMs.”
Daniel Wickberg Jul 28, 2022 ▶ 1:51
Assertion Not publicly verifiable
UpSales Jumped From 600 to 1,800 Customers Overnight After Partner Migration
“And a lot of these very tiny customers migrated to up sales a while back to some, we went from like 600 customers to 1800 customers almost overnight.”
Daniel Wickberg Jul 28, 2022 ▶ 2:39
Assertion Supported
UpSales Is Growing ARR by 30% to 35% on $9.8M Base
“So one year ago we were at 9.8. So we're growing the error at around, you know, between 30 and 35%.”
Daniel Wickberg Jul 28, 2022 ▶ 4:21
Insight
Custom Consulting Funded UpSales' Early Survival But Slowed Down Scalability
“And I think you know, the early days, we never raised any capital. So you know, our first 10 years were like, Barely breaking even, you know, struggling to pay the bills every month. So we used to do a lot of customized consulting stuff for our clients. And I …”
Daniel Wickberg Jul 28, 2022 ▶ 5:38
Assertion Supported
UpSales Raised $3M in Its IPO But Never Needed to Spend It
“Yeah, so we did a secondary, a pre-IPO, which was around four to five million dollars. And then in the IPO, we raised around three million dollars but we never actually used that money because we had a debt.”
Daniel Wickberg Jul 28, 2022 ▶ 6:20
Disclosure
Wickberg Sold 10% of UpSales in a Pre-IPO Secondary Transaction
“So I sold 10% in, in the pre-IPO. And I had a partner our former CEO who was CEO for almost five years. He had seven or eight percent. So, so the total was like, 18% that was sold in the pre-IPO.”
Daniel Wickberg Jul 28, 2022 ▶ 7:14
Disclosure
Going Public Was the Easiest Way to Preserve Majority Shareholder Control
“Going public and, you know, I'm still the majority shareholder turned out to be like the easiest way to continue running the business the way I want to do it.”
Daniel Wickberg Jul 28, 2022 ▶ 10:57
Assertion Not publicly verifiable
UpSales Currently Maintains Net Dollar Retention Around 115% to 120%
“I think we are today at around one 15, one 20, somewhere around that.”
Daniel Wickberg Jul 28, 2022 ▶ 12:08
Assertion Not publicly verifiable
Customer Expansion Drives Up to 70% of UpSales' Net New ARR
“I mean, it used to be like fifty-fifty of the new ARR, net new ARR came from new customers and expansion. Now because of all the kind of the smaller customers we inherited a while back, now it's around 60, 70% comes from expansions.”
Daniel Wickberg Jul 28, 2022 ▶ 12:17
Insight
Why UpSales Deliberately Reduces Initial Deal Sizes for New Customers
“We almost try to kind of decrease the deal size when the customer joins us, because it makes everything easier and it decreases the risk for the customer as well. So, so yeah, we just try to add as many customers as we can and then grow them over time.”
Daniel Wickberg Jul 28, 2022 ▶ 14:06
Assertion Supported
UpSales Sustains 35% Annual Revenue Growth With 25%–30% FCF Margins
“I mean, we're very proud of, you know, growing revenues 35% per year with, like 25, 30% free cash flow margin.”
Daniel Wickberg Jul 28, 2022 ▶ 14:46
Assertion Supported
Why Fast-Growing Tech Company UpSales Pays a Dividend to Its Shareholders
“We're one of those weird, fast growing tech companies who also pays a dividend.”
Daniel Wickberg Jul 28, 2022 ▶ 15:12
Assertion Supported
UpSales Trades at 7.5x to 8x EV/ARR With Zero Debt
“It used to be 200 in, in January before everything blew up, but I mean, I think we're net cash. We don't have any debt. So I think enterprise value ARR multiple is around 7.5 or eight, which is lower than a lot of our peers, I would say.”
Daniel Wickberg Jul 28, 2022 ▶ 15:31
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