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Jun 6, 2020 · 24m · top-founders

"He Raised $900k And Sold For $1.8m... Why? "

Anders Fredriksson · 11m spoken Nathan Latka · 9m spoken Eric Yuan · 4s spoken Vivek Bhaskaran · 2s spoken
0:00 / 0:00

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In this interview with Nathan Latka, serial entrepreneur Anders Fredriksson details the eight-year journey of B2B sales automation platform Proleads and explains why he chose a $1.8 million strategic acquisition over raising further venture capital.

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 44.3% of the talking time here. How this is scored →

Nathan as informed peer 6.3 Guest teaching 2.0 Guest disagreement 1.6 Nathan pushing back 5.1
05100:0010:0020:001:48–4:47 · Nathan as informed peer 6/10 Introducing Anders Fredriksson and Proleads Company History Nathan pulls specific numbers from Anders' prior 2017 appearance on the show to establish context on customer count and ARR. Anders willingly explains Proleads' product concept and uses a race car metaphor to describe their customer enablement struggles.4:47–9:00 · Nathan as informed peer 6/10 High Customer Churn and Rebranding as Hexa Nathan presses Anders to quantify vague statements like 'not good growth' and extract specific churn figures. He also probes into the exact terms and rationale behind Proleads' asset acquisition of Brisk.9:02–11:02 · Nathan as informed peer 6/10 Alchemist Accelerator Funding and Deal Capital Structure Nathan interrupts to keep the interview on schedule and directly cross-examines Anders' cash balance, accelerator funding, and total capital raised.11:03–15:43 · Nathan as informed peer 7/10 Strategic Alignment and OutboundWorks Acquisition Talks Nathan challenges Anders aggressively when Anders claims not to remember his company's ARR prior to acquisition, catching Anders confusing monthly revenue with ARR and forcing him to clarify.15:43–19:52 · Nathan as informed peer 8/10 Acquisition Multiples, Valuation, and Deal Structure Nathan digs into deal multiples, deducing valuation from total raised capital, and checks OutboundWorks founder's LinkedIn live on the call to press on unannounced acquisition details.19:53–22:36 · Nathan as informed peer 7/10 Founder Decisions: Strategic Acquisition vs. Startup Grind Nathan candidly breaks down the meager financial payout a founder receives after paying back investors in a low-multiple exit, while Anders calmly explains the rational tradeoff between years of startup grind and selling.22:36–23:47 · Nathan as informed peer 4/10 Famous Five Rapid-Fire Questions and Personal Reflections Nathan conducts his standard Famous Five rapid-fire questions, celebrating Anders' upcoming child, and wraps up with an executive summary of the episode's deal mechanics.1:48–4:47 · Guest teaching 1/10 Introducing Anders Fredriksson and Proleads Company History Nathan pulls specific numbers from Anders' prior 2017 appearance on the show to establish context on customer count and ARR. Anders willingly explains Proleads' product concept and uses a race car metaphor to describe their customer enablement struggles.4:47–9:00 · Guest teaching 2/10 High Customer Churn and Rebranding as Hexa Nathan presses Anders to quantify vague statements like 'not good growth' and extract specific churn figures. He also probes into the exact terms and rationale behind Proleads' asset acquisition of Brisk.9:02–11:02 · Guest teaching 2/10 Alchemist Accelerator Funding and Deal Capital Structure Nathan interrupts to keep the interview on schedule and directly cross-examines Anders' cash balance, accelerator funding, and total capital raised.11:03–15:43 · Guest teaching 3/10 Strategic Alignment and OutboundWorks Acquisition Talks Nathan challenges Anders aggressively when Anders claims not to remember his company's ARR prior to acquisition, catching Anders confusing monthly revenue with ARR and forcing him to clarify.15:43–19:52 · Guest teaching 2/10 Acquisition Multiples, Valuation, and Deal Structure Nathan digs into deal multiples, deducing valuation from total raised capital, and checks OutboundWorks founder's LinkedIn live on the call to press on unannounced acquisition details.19:53–22:36 · Guest teaching 4/10 Founder Decisions: Strategic Acquisition vs. Startup Grind Nathan candidly breaks down the meager financial payout a founder receives after paying back investors in a low-multiple exit, while Anders calmly explains the rational tradeoff between years of startup grind and selling.22:36–23:47 · Guest teaching 0/10 Famous Five Rapid-Fire Questions and Personal Reflections Nathan conducts his standard Famous Five rapid-fire questions, celebrating Anders' upcoming child, and wraps up with an executive summary of the episode's deal mechanics.1:48–4:47 · Guest disagreement 1/10 Introducing Anders Fredriksson and Proleads Company History Nathan pulls specific numbers from Anders' prior 2017 appearance on the show to establish context on customer count and ARR. Anders willingly explains Proleads' product concept and uses a race car metaphor to describe their customer enablement struggles.4:47–9:00 · Guest disagreement 2/10 High Customer Churn and Rebranding as Hexa Nathan presses Anders to quantify vague statements like 'not good growth' and extract specific churn figures. He also probes into the exact terms and rationale behind Proleads' asset acquisition of Brisk.9:02–11:02 · Guest disagreement 1/10 Alchemist Accelerator Funding and Deal Capital Structure Nathan interrupts to keep the interview on schedule and directly cross-examines Anders' cash balance, accelerator funding, and total capital raised.11:03–15:43 · Guest disagreement 2/10 Strategic Alignment and OutboundWorks Acquisition Talks Nathan challenges Anders aggressively when Anders claims not to remember his company's ARR prior to acquisition, catching Anders confusing monthly revenue with ARR and forcing him to clarify.15:43–19:52 · Guest disagreement 3/10 Acquisition Multiples, Valuation, and Deal Structure Nathan digs into deal multiples, deducing valuation from total raised capital, and checks OutboundWorks founder's LinkedIn live on the call to press on unannounced acquisition details.19:53–22:36 · Guest disagreement 2/10 Founder Decisions: Strategic Acquisition vs. Startup Grind Nathan candidly breaks down the meager financial payout a founder receives after paying back investors in a low-multiple exit, while Anders calmly explains the rational tradeoff between years of startup grind and selling.22:36–23:47 · Guest disagreement 0/10 Famous Five Rapid-Fire Questions and Personal Reflections Nathan conducts his standard Famous Five rapid-fire questions, celebrating Anders' upcoming child, and wraps up with an executive summary of the episode's deal mechanics.1:48–4:47 · Nathan pushing back 3/10 Introducing Anders Fredriksson and Proleads Company History Nathan pulls specific numbers from Anders' prior 2017 appearance on the show to establish context on customer count and ARR. Anders willingly explains Proleads' product concept and uses a race car metaphor to describe their customer enablement struggles.4:47–9:00 · Nathan pushing back 5/10 High Customer Churn and Rebranding as Hexa Nathan presses Anders to quantify vague statements like 'not good growth' and extract specific churn figures. He also probes into the exact terms and rationale behind Proleads' asset acquisition of Brisk.9:02–11:02 · Nathan pushing back 6/10 Alchemist Accelerator Funding and Deal Capital Structure Nathan interrupts to keep the interview on schedule and directly cross-examines Anders' cash balance, accelerator funding, and total capital raised.11:03–15:43 · Nathan pushing back 8/10 Strategic Alignment and OutboundWorks Acquisition Talks Nathan challenges Anders aggressively when Anders claims not to remember his company's ARR prior to acquisition, catching Anders confusing monthly revenue with ARR and forcing him to clarify.15:43–19:52 · Nathan pushing back 7/10 Acquisition Multiples, Valuation, and Deal Structure Nathan digs into deal multiples, deducing valuation from total raised capital, and checks OutboundWorks founder's LinkedIn live on the call to press on unannounced acquisition details.19:53–22:36 · Nathan pushing back 6/10 Founder Decisions: Strategic Acquisition vs. Startup Grind Nathan candidly breaks down the meager financial payout a founder receives after paying back investors in a low-multiple exit, while Anders calmly explains the rational tradeoff between years of startup grind and selling.22:36–23:47 · Nathan pushing back 1/10 Famous Five Rapid-Fire Questions and Personal Reflections Nathan conducts his standard Famous Five rapid-fire questions, celebrating Anders' upcoming child, and wraps up with an executive summary of the episode's deal mechanics.

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

0:00 · Nathan 72.9% · guest 27.1%0:00 · Nathan 72.9% · guest 27.1%3:00 · Nathan 23.3% · guest 76.7%3:00 · Nathan 23.3% · guest 76.7%6:00 · Nathan 17.7% · guest 82.3%6:00 · Nathan 17.7% · guest 82.3%9:00 · Nathan 36.5% · guest 63.5%9:00 · Nathan 36.5% · guest 63.5%12:00 · Nathan 48.4% · guest 51.6%12:00 · Nathan 48.4% · guest 51.6%15:00 · Nathan 53.9% · guest 46.1%15:00 · Nathan 53.9% · guest 46.1%18:00 · Nathan 44.6% · guest 55.4%18:00 · Nathan 44.6% · guest 55.4%21:00 · Nathan 44.3% · guest 55.7%21:00 · Nathan 44.3% · guest 55.7%24:00 · Nathan 100% · guest 0%24:00 · Nathan 100% · guest 0%
Sharpest disagreement ▶ 18:10 Anders asserts confidentiality regarding undisclosed acquirer

Anders firmly pushes back against Nathan's probing regarding who acquired OutboundWorks, refusing to disclose confidential details ahead of an unreleased press release.

 Hardest push from Nathan ▶ 13:21 Nathan refuses Anders' claim of not remembering pre-sale ARR

Nathan directly challenges Anders for saying he cannot recall his exit ARR from only 12 to 24 months earlier, insisting it is a metric any founder would know by heart.

 Biggest teaching moment ▶ 20:30 Anders breaks down the real founder math behind small exits

Anders reframes Nathan's harsh financial critique by explaining the realistic founder calculus between several more years of uncertain grinding versus de-risking through strategic M&A.

 Nathan holds their own ▶ 14:02 Nathan computes ARR and untangles Anders' revenue math

Nathan leverages historical data and quick mental math to demonstrate why Anders' estimated ARR was inconsistent, correcting Anders on the difference between MRR and ARR.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Anders Fredriksson and Proleads Company History 6113 Nathan pulls specific numbers from Anders' prior 2017 appearance on the show to establish context on customer count and ARR. Anders willingly explains Proleads' product concept and uses a race car metaphor to describe their customer enablement struggles.
High Customer Churn and Rebranding as Hexa 6225 Nathan presses Anders to quantify vague statements like 'not good growth' and extract specific churn figures. He also probes into the exact terms and rationale behind Proleads' asset acquisition of Brisk.
Alchemist Accelerator Funding and Deal Capital Structure 6216 Nathan interrupts to keep the interview on schedule and directly cross-examines Anders' cash balance, accelerator funding, and total capital raised.
Strategic Alignment and OutboundWorks Acquisition Talks 7328 Nathan challenges Anders aggressively when Anders claims not to remember his company's ARR prior to acquisition, catching Anders confusing monthly revenue with ARR and forcing him to clarify.
Acquisition Multiples, Valuation, and Deal Structure 8237 Nathan digs into deal multiples, deducing valuation from total raised capital, and checks OutboundWorks founder's LinkedIn live on the call to press on unannounced acquisition details.
Founder Decisions: Strategic Acquisition vs. Startup Grind 7426 Nathan candidly breaks down the meager financial payout a founder receives after paying back investors in a low-multiple exit, while Anders calmly explains the rational tradeoff between years of startup grind and selling.
Famous Five Rapid-Fire Questions and Personal Reflections 4001 Nathan conducts his standard Famous Five rapid-fire questions, celebrating Anders' upcoming child, and wraps up with an executive summary of the episode's deal mechanics.

Statements from this episode (13)

Assertion Partly supported
Proleads launched in 2010 and operated for eight years before acquisition
“So the first initial launch of what eventually became probably say that was in 2010. So eight years of struggling.”
Anders Fredriksson Jun 6, 2020 ▶ 2:35
Disclosure
Proleads sold because its product was too complex for junior SDRs
“We had a major problem, which was part of the decision to sell, actually. So the way I like to describe it is that we developed this sort of, imagine that we built this perfect race car that was like, you know, race tune Ferrari that was perfect for driving on…”
Anders Fredriksson Jun 6, 2020 ▶ 3:57
Assertion Not checkable as stated
Proleads suffered a brutal 50% annual customer churn rate
“Over the whole year, maybe like, 50% of the customers we sold to churn, so like terrible.”
Anders Fredriksson Jun 6, 2020 ▶ 5:22
Disclosure
Proleads rebranded to Hexa and made a small acquisition before selling
“Right before the acquisition, we actually sort of revamped the whole company rebranded it as Hexa. We brought on a new co-founder and we also actually made a small acquisition in that process.”
Anders Fredriksson Jun 6, 2020 ▶ 6:01
Disclosure
Proleads acquired Brisk's technology assets in a six-figure deal
“It was in a six figure deal.”
Anders Fredriksson Jun 6, 2020 ▶ 7:22
Disclosure
Proleads raised $150K to $200K from the Alchemist Accelerator
“So we joined the Alchemist Accelerator, and we got in an extra, I think it was, 152 hundred, something like that.”
Anders Fredriksson Jun 6, 2020 ▶ 9:24
Disclosure
Proleads spent $25K to $50K in cash to acquire Brisk's assets
“I think it was, I don't know if that's a number is actually official though, but I would say maybe, maybe in the 25 to 50 range.”
Anders Fredriksson Jun 6, 2020 ▶ 10:22
Disclosure
Proleads raised $880K to $900K in total outside capital
“Yeah, so we had raised, we raised the total of 880 or 900 or so for total for pro leads.”
Anders Fredriksson Jun 6, 2020 ▶ 10:46
Disclosure
Fredriksson chose to sell Proleads rather than raise an independent round
“Eventually we decided that the best chance for ourselves for a good outcome in the end would be to join forces with Alpine works instead of raising the capital and running our own.”
Anders Fredriksson Jun 6, 2020 ▶ 12:37
Assertion Not checkable as stated
Proleads generated $200K to $500K in ARR before its 2018 acquisition
“Let's just say that we were somewhere in the 200 to 500,000 dollar ARR.”
Anders Fredriksson Jun 6, 2020 ▶ 14:42
Disclosure
Proleads benchmarked its acquisition price against venture term sheets, not revenue
“Yeah, not a revenue. It was more because we were sort of talking with, because we were talking with investors, it was more that like, okay, we have this in the one hand we have, like, we have the investment from investors in the one hand and we have the acquis…”
Anders Fredriksson Jun 6, 2020 ▶ 15:22
Assertion Not publicly verifiable
Proleads sold for more than double its $900K in raised capital
“I can't say the exact amount, but it was, More than two X the amount.”
Anders Fredriksson Jun 6, 2020 ▶ 15:58
Disclosure
The Proleads acquisition payout was structured mostly in cash
“So it was mostly cash, but there was also stock.”
Anders Fredriksson Jun 6, 2020 ▶ 16:24
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