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May 30, 2018 · 19m · top-founders

1040 To Get Rich, Don't Need $1b Exit, She Has 4 Exits Across 10 Companies

Roz Lemieux · 10m spoken Nathan Latka · 7m 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 episode of The Top Entrepreneurs, host Nathan Latka interviews Roz Lemieux on building and selling Attentive.ly to Blackbaud for over $3 million, highlighting the power of executing realistic multi-million-dollar exits rather than chasing unicorn valuations.

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 41.6% of the talking time here. How this is scored →

Nathan as informed peer 4.4 Guest teaching 3.1 Guest disagreement 1.6 Nathan pushing back 3.0
05100:0010:001:16–3:28 · Nathan as informed peer 5/10 Attentive.ly Product Overview and SaaS Revenue Model Nathan seeks to clarify whether the platform is a crowdfunding tool like Kickstarter or a B2B SaaS model. Roz corrects his framing, explaining it functions as a social listening and CRM add-on for nonprofits.3:29–7:43 · Nathan as informed peer 6/10 Agency Origins, Landing Page Validation, and Seed Funding Nathan challenges Roz on why she stayed post-sale given conventional wisdom on founder wealth, but Roz reframes the discussion away from binary billion-dollar exits toward sustainable multi-million exits.7:43–10:35 · Nathan as informed peer 5/10 API Dependency Risks, Undercapitalization, and Exit Motivations Nathan calculates run rates based on deal size and customer count while probing exit drivers. Roz candidly breaks down the operational traps of undercapitalization and building atop third-party APIs.10:38–12:41 · Nathan as informed peer 6/10 Acquisition Valuation and Outbound Sales Methodologies Nathan drills into valuation benchmarks and liquidation preference waterfalls to ensure common holders profited. The two banter collaboratively about low-cost conference networking tactics.12:42–16:40 · Nathan as informed peer 7/10 Churn Dynamics and Managing a Distributed Remote Team Nathan presses repeatedly on churn benchmarks and CAC payback periods, highlighting the SaaS pricing 'death valley' when deal sizes require salespeople but cannot support them.16:40–18:50 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions Nathan guides Roz through standard rapid-fire questions, nudging her to narrow down multiple book recommendations to one.18:50–19:38 · Nathan as informed peer 0/10 Episode Summary and Key Entrepreneurial Takeaways Nathan delivers a solo outro recapping Roz's track record of hitting doubles across four exits and ten companies.1:16–3:28 · Guest teaching 4/10 Attentive.ly Product Overview and SaaS Revenue Model Nathan seeks to clarify whether the platform is a crowdfunding tool like Kickstarter or a B2B SaaS model. Roz corrects his framing, explaining it functions as a social listening and CRM add-on for nonprofits.3:29–7:43 · Guest teaching 5/10 Agency Origins, Landing Page Validation, and Seed Funding Nathan challenges Roz on why she stayed post-sale given conventional wisdom on founder wealth, but Roz reframes the discussion away from binary billion-dollar exits toward sustainable multi-million exits.7:43–10:35 · Guest teaching 5/10 API Dependency Risks, Undercapitalization, and Exit Motivations Nathan calculates run rates based on deal size and customer count while probing exit drivers. Roz candidly breaks down the operational traps of undercapitalization and building atop third-party APIs.10:38–12:41 · Guest teaching 2/10 Acquisition Valuation and Outbound Sales Methodologies Nathan drills into valuation benchmarks and liquidation preference waterfalls to ensure common holders profited. The two banter collaboratively about low-cost conference networking tactics.12:42–16:40 · Guest teaching 4/10 Churn Dynamics and Managing a Distributed Remote Team Nathan presses repeatedly on churn benchmarks and CAC payback periods, highlighting the SaaS pricing 'death valley' when deal sizes require salespeople but cannot support them.16:40–18:50 · Guest teaching 2/10 The Famous Five Rapid-Fire Questions Nathan guides Roz through standard rapid-fire questions, nudging her to narrow down multiple book recommendations to one.18:50–19:38 · Guest teaching 0/10 Episode Summary and Key Entrepreneurial Takeaways Nathan delivers a solo outro recapping Roz's track record of hitting doubles across four exits and ten companies.1:16–3:28 · Guest disagreement 2/10 Attentive.ly Product Overview and SaaS Revenue Model Nathan seeks to clarify whether the platform is a crowdfunding tool like Kickstarter or a B2B SaaS model. Roz corrects his framing, explaining it functions as a social listening and CRM add-on for nonprofits.3:29–7:43 · Guest disagreement 4/10 Agency Origins, Landing Page Validation, and Seed Funding Nathan challenges Roz on why she stayed post-sale given conventional wisdom on founder wealth, but Roz reframes the discussion away from binary billion-dollar exits toward sustainable multi-million exits.7:43–10:35 · Guest disagreement 1/10 API Dependency Risks, Undercapitalization, and Exit Motivations Nathan calculates run rates based on deal size and customer count while probing exit drivers. Roz candidly breaks down the operational traps of undercapitalization and building atop third-party APIs.10:38–12:41 · Guest disagreement 1/10 Acquisition Valuation and Outbound Sales Methodologies Nathan drills into valuation benchmarks and liquidation preference waterfalls to ensure common holders profited. The two banter collaboratively about low-cost conference networking tactics.12:42–16:40 · Guest disagreement 2/10 Churn Dynamics and Managing a Distributed Remote Team Nathan presses repeatedly on churn benchmarks and CAC payback periods, highlighting the SaaS pricing 'death valley' when deal sizes require salespeople but cannot support them.16:40–18:50 · Guest disagreement 1/10 The Famous Five Rapid-Fire Questions Nathan guides Roz through standard rapid-fire questions, nudging her to narrow down multiple book recommendations to one.18:50–19:38 · Guest disagreement 0/10 Episode Summary and Key Entrepreneurial Takeaways Nathan delivers a solo outro recapping Roz's track record of hitting doubles across four exits and ten companies.1:16–3:28 · Nathan pushing back 3/10 Attentive.ly Product Overview and SaaS Revenue Model Nathan seeks to clarify whether the platform is a crowdfunding tool like Kickstarter or a B2B SaaS model. Roz corrects his framing, explaining it functions as a social listening and CRM add-on for nonprofits.3:29–7:43 · Nathan pushing back 4/10 Agency Origins, Landing Page Validation, and Seed Funding Nathan challenges Roz on why she stayed post-sale given conventional wisdom on founder wealth, but Roz reframes the discussion away from binary billion-dollar exits toward sustainable multi-million exits.7:43–10:35 · Nathan pushing back 3/10 API Dependency Risks, Undercapitalization, and Exit Motivations Nathan calculates run rates based on deal size and customer count while probing exit drivers. Roz candidly breaks down the operational traps of undercapitalization and building atop third-party APIs.10:38–12:41 · Nathan pushing back 3/10 Acquisition Valuation and Outbound Sales Methodologies Nathan drills into valuation benchmarks and liquidation preference waterfalls to ensure common holders profited. The two banter collaboratively about low-cost conference networking tactics.12:42–16:40 · Nathan pushing back 6/10 Churn Dynamics and Managing a Distributed Remote Team Nathan presses repeatedly on churn benchmarks and CAC payback periods, highlighting the SaaS pricing 'death valley' when deal sizes require salespeople but cannot support them.16:40–18:50 · Nathan pushing back 2/10 The Famous Five Rapid-Fire Questions Nathan guides Roz through standard rapid-fire questions, nudging her to narrow down multiple book recommendations to one.18:50–19:38 · Nathan pushing back 0/10 Episode Summary and Key Entrepreneurial Takeaways Nathan delivers a solo outro recapping Roz's track record of hitting doubles across four exits and ten companies.

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

0:00 · Nathan 53% · guest 47%0:00 · Nathan 53% · guest 47%3:00 · Nathan 24% · guest 76%3:00 · Nathan 24% · guest 76%6:00 · Nathan 31.9% · guest 68.1%6:00 · Nathan 31.9% · guest 68.1%9:00 · Nathan 62.5% · guest 37.5%9:00 · Nathan 62.5% · guest 37.5%12:00 · Nathan 39% · guest 61%12:00 · Nathan 39% · guest 61%15:00 · Nathan 23.6% · guest 76.4%15:00 · Nathan 23.6% · guest 76.4%18:00 · Nathan 70% · guest 30%18:00 · Nathan 70% · guest 30%
Sharpest disagreement ▶ 6:25 Challenging the filthy rich versus broke binary

Roz explicitly pushes back against the podcast's opening premise, arguing that entrepreneurship is often about steady moderate exits rather than extreme billion-dollar outcomes.

 Hardest push from Nathan ▶ 14:00 Pushing on customer acquisition payback visibility

Nathan refuses to let go of the unit economics inquiry, asking how acquisition spending decisions could be justified without tracking payback duration.

 Biggest teaching moment ▶ 8:35 Educating on third-party API vulnerabilities

Roz provides an insightful breakdown of how simultaneous API overhauls from major platforms drained engineering resources and forced strategic M&A.

 Nathan holds their own ▶ 15:45 Diagnosing the mid-market SaaS pricing death valley

Nathan synthesizes SaaS economics theory to explain why an $8,000 ACV represents a dangerous middle ground for high-touch sales organizations.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Attentive.ly Product Overview and SaaS Revenue Model 5423 Nathan seeks to clarify whether the platform is a crowdfunding tool like Kickstarter or a B2B SaaS model. Roz corrects his framing, explaining it functions as a social listening and CRM add-on for nonprofits.
Agency Origins, Landing Page Validation, and Seed Funding 6544 Nathan challenges Roz on why she stayed post-sale given conventional wisdom on founder wealth, but Roz reframes the discussion away from binary billion-dollar exits toward sustainable multi-million exits.
API Dependency Risks, Undercapitalization, and Exit Motivations 5513 Nathan calculates run rates based on deal size and customer count while probing exit drivers. Roz candidly breaks down the operational traps of undercapitalization and building atop third-party APIs.
Acquisition Valuation and Outbound Sales Methodologies 6213 Nathan drills into valuation benchmarks and liquidation preference waterfalls to ensure common holders profited. The two banter collaboratively about low-cost conference networking tactics.
Churn Dynamics and Managing a Distributed Remote Team 7426 Nathan presses repeatedly on churn benchmarks and CAC payback periods, highlighting the SaaS pricing 'death valley' when deal sizes require salespeople but cannot support them.
The Famous Five Rapid-Fire Questions 2212 Nathan guides Roz through standard rapid-fire questions, nudging her to narrow down multiple book recommendations to one.
Episode Summary and Key Entrepreneurial Takeaways 0000 Nathan delivers a solo outro recapping Roz's track record of hitting doubles across four exits and ten companies.

Statements from this episode (13)

Disclosure
Lemieux: Attentive.ly raised about $2.1 million in total pre-acquisition funding
“Oh, in total a couple million. I want to say 2.1.”
Roz Lemieux May 30, 2018 ▶ 5:17
Assertion Supported
Lemieux: Attentive.ly Had 11 Employees When Acquired by Blackbaud
“We were only 11 people when we were acquired.”
Roz Lemieux May 30, 2018 ▶ 6:04
Assertion Not checkable as stated
Lemieux: Founded 10+ Companies and Reached 4 Exits With Husband
“I think between us, we've started 10 plus companies and had four exits.”
Roz Lemieux May 30, 2018 ▶ 6:49
Insight
Lemieux: Multiple Small Startup Exits Provide Total Freedom
“Every exit isn't a billion dollar exit, right? But you get enough of these little one and two base hits, and you can have the freedom to do whatever you want to.”
Roz Lemieux May 30, 2018 ▶ 7:15
Disclosure
Lemieux: Attentive.ly served about 120 customers at acquisition
“About a 120.”
Roz Lemieux May 30, 2018 ▶ 7:49
Disclosure
Lemieux: Attentive.ly raised too little money to withstand platform API changes
“One of them is we raised too little money. And when we had a, you know, six month period where MailChimp changed their API and Facebook completely where you're at their API and full content, like every tool that we used that sucked up all our dev resources, an…”
Roz Lemieux May 30, 2018 ▶ 8:56
Assertion Supported
Lemieux: Attentive.ly sold for more than $3 million
“More.”
Roz Lemieux May 30, 2018 ▶ 10:42
Insight
Latka: Building on partner APIs creates startup acquisition demand
“If you start thinking about an exit, having channel partners is a great place to start in terms of trying to drum up demand for your company, because you're already built on their API, hopefully adding value”
Nathan Latka May 30, 2018 ▶ 12:23
Assertion Not checkable as stated
Lemieux: Attentive.ly experienced over 10% annual customer churn prior to sale
“Not per month, no, but certainly more than 10% per year, which, you know, on the very high end when you're nailing it.”
Roz Lemieux May 30, 2018 ▶ 13:04
Disclosure
Lemieux: Integration-driven churn motivated Attentive.ly's acquisition
“And actually for part of the motivation with the acquisition too was people were churning because the integrations weren't strong enough.”
Roz Lemieux May 30, 2018 ▶ 13:12
Assertion Not checkable as stated
Lemieux: Attentive.ly had a 3 to 4 month sales cycle for $8,000 deals
“It was I want to say three or four months. So, you know, for an 8000 dollar deal, it wasn't optimal.”
Roz Lemieux May 30, 2018 ▶ 15:14
Insight
Lemieux: An $8,000 ACV is difficult for high-touch, commission-based B2B sales
“If you've got a product, that's a true B to B sale that takes a salesperson and you're moving things with, you know, commission based You know, that deal size is, is tough.”
Roz Lemieux May 30, 2018 ▶ 15:38
Assertion Not publicly verifiable
Lemieux: Post-acquisition, Attentive.ly switched pricing from matches to total CRM contacts
“We changed the price structure. So now it's tied to it's a little in the weeds, but it was tied to match. So how many social matches were actually listening to in the product? And now it's tied to your overall number of contacts in your CRM because it's being …”
Roz Lemieux May 30, 2018 ▶ 16:09
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