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Dec 8, 2018 · 19m · top-founders

1232 I should have sold my first company sooner, now LeadDyno $1m+

Brett Owens · 10m spoken Nathan Latka · 6m 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 LeadDyno co-founder Brett Owens on scaling his bootstrapped affiliate marketing software past $1 million in ARR. Owens breaks down their SaaS unit economics, churn mitigation tactics, remote team structure, and the critical lessons learned from a previous failed venture.

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 38.2% of the talking time here. How this is scored →

Nathan as informed peer 5.0 Guest teaching 2.2 Guest disagreement 1.0 Nathan pushing back 2.7
05100:0010:001:17–3:26 · Nathan as informed peer 4/10 Guest Welcome and Early LeadDyno Milestones Nathan opens by checking Brett's early timeline and clarifying the distinction between initial MRR and customer counts. Brett collaboratively details the initial three cofounders and bootstrapping history.3:28–6:03 · Nathan as informed peer 6/10 Product Value Proposition, Pricing, and Acquisition Channels Nathan quickly runs the mental math on ARPU and customer volume to calculate monthly run rate and ARR. Brett outlines LeadDyno's product differentiation and acquisition channels via app store integrations.6:03–8:37 · Nathan as informed peer 5/10 Host Note on Podcast Scheduling and Early Access Nathan presses Brett on competitor differentiation and drills into monthly logo churn numbers. Brett transparently acknowledges high single-digit churn driven by customer business mortality in e-commerce.8:41–12:57 · Nathan as informed peer 7/10 Sponsor Message: Gusto Payroll and HR Platform Following the sponsor break, Nathan computes customer lifetime from the 8% monthly churn rate and challenges Brett to test upfront annual pricing. Brett admits they have only tested monthly pricing and shares past freemium lessons.12:59–17:02 · Nathan as informed peer 4/10 Team Distribution and Philosophy on Bootstrapping Nathan explores the remote team structure and conducts the Famous Five questionnaire, pushing slightly on whether dedicated live chat headcount is worth the payroll cost.17:03–18:17 · Nathan as informed peer 4/10 Lessons from Past Startup Mistakes and Delayed Exits Brett reflects candidly on losing $300k on his first business before selling at a loss. Nathan validates the painful lesson of knowing when to exit a stagnant business early.1:17–3:26 · Guest teaching 2/10 Guest Welcome and Early LeadDyno Milestones Nathan opens by checking Brett's early timeline and clarifying the distinction between initial MRR and customer counts. Brett collaboratively details the initial three cofounders and bootstrapping history.3:28–6:03 · Guest teaching 1/10 Product Value Proposition, Pricing, and Acquisition Channels Nathan quickly runs the mental math on ARPU and customer volume to calculate monthly run rate and ARR. Brett outlines LeadDyno's product differentiation and acquisition channels via app store integrations.6:03–8:37 · Guest teaching 3/10 Host Note on Podcast Scheduling and Early Access Nathan presses Brett on competitor differentiation and drills into monthly logo churn numbers. Brett transparently acknowledges high single-digit churn driven by customer business mortality in e-commerce.8:41–12:57 · Guest teaching 2/10 Sponsor Message: Gusto Payroll and HR Platform Following the sponsor break, Nathan computes customer lifetime from the 8% monthly churn rate and challenges Brett to test upfront annual pricing. Brett admits they have only tested monthly pricing and shares past freemium lessons.12:59–17:02 · Guest teaching 2/10 Team Distribution and Philosophy on Bootstrapping Nathan explores the remote team structure and conducts the Famous Five questionnaire, pushing slightly on whether dedicated live chat headcount is worth the payroll cost.17:03–18:17 · Guest teaching 3/10 Lessons from Past Startup Mistakes and Delayed Exits Brett reflects candidly on losing $300k on his first business before selling at a loss. Nathan validates the painful lesson of knowing when to exit a stagnant business early.1:17–3:26 · Guest disagreement 1/10 Guest Welcome and Early LeadDyno Milestones Nathan opens by checking Brett's early timeline and clarifying the distinction between initial MRR and customer counts. Brett collaboratively details the initial three cofounders and bootstrapping history.3:28–6:03 · Guest disagreement 1/10 Product Value Proposition, Pricing, and Acquisition Channels Nathan quickly runs the mental math on ARPU and customer volume to calculate monthly run rate and ARR. Brett outlines LeadDyno's product differentiation and acquisition channels via app store integrations.6:03–8:37 · Guest disagreement 1/10 Host Note on Podcast Scheduling and Early Access Nathan presses Brett on competitor differentiation and drills into monthly logo churn numbers. Brett transparently acknowledges high single-digit churn driven by customer business mortality in e-commerce.8:41–12:57 · Guest disagreement 1/10 Sponsor Message: Gusto Payroll and HR Platform Following the sponsor break, Nathan computes customer lifetime from the 8% monthly churn rate and challenges Brett to test upfront annual pricing. Brett admits they have only tested monthly pricing and shares past freemium lessons.12:59–17:02 · Guest disagreement 1/10 Team Distribution and Philosophy on Bootstrapping Nathan explores the remote team structure and conducts the Famous Five questionnaire, pushing slightly on whether dedicated live chat headcount is worth the payroll cost.17:03–18:17 · Guest disagreement 1/10 Lessons from Past Startup Mistakes and Delayed Exits Brett reflects candidly on losing $300k on his first business before selling at a loss. Nathan validates the painful lesson of knowing when to exit a stagnant business early.1:17–3:26 · Nathan pushing back 2/10 Guest Welcome and Early LeadDyno Milestones Nathan opens by checking Brett's early timeline and clarifying the distinction between initial MRR and customer counts. Brett collaboratively details the initial three cofounders and bootstrapping history.3:28–6:03 · Nathan pushing back 2/10 Product Value Proposition, Pricing, and Acquisition Channels Nathan quickly runs the mental math on ARPU and customer volume to calculate monthly run rate and ARR. Brett outlines LeadDyno's product differentiation and acquisition channels via app store integrations.6:03–8:37 · Nathan pushing back 4/10 Host Note on Podcast Scheduling and Early Access Nathan presses Brett on competitor differentiation and drills into monthly logo churn numbers. Brett transparently acknowledges high single-digit churn driven by customer business mortality in e-commerce.8:41–12:57 · Nathan pushing back 4/10 Sponsor Message: Gusto Payroll and HR Platform Following the sponsor break, Nathan computes customer lifetime from the 8% monthly churn rate and challenges Brett to test upfront annual pricing. Brett admits they have only tested monthly pricing and shares past freemium lessons.12:59–17:02 · Nathan pushing back 2/10 Team Distribution and Philosophy on Bootstrapping Nathan explores the remote team structure and conducts the Famous Five questionnaire, pushing slightly on whether dedicated live chat headcount is worth the payroll cost.17:03–18:17 · Nathan pushing back 2/10 Lessons from Past Startup Mistakes and Delayed Exits Brett reflects candidly on losing $300k on his first business before selling at a loss. Nathan validates the painful lesson of knowing when to exit a stagnant business early.

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

0:00 · Nathan 60.3% · guest 39.7%0:00 · Nathan 60.3% · guest 39.7%3:00 · Nathan 20.5% · guest 79.5%3:00 · Nathan 20.5% · guest 79.5%6:00 · Nathan 29.3% · guest 70.7%6:00 · Nathan 29.3% · guest 70.7%9:00 · Nathan 65.1% · guest 34.9%9:00 · Nathan 65.1% · guest 34.9%12:00 · Nathan 20.4% · guest 79.6%12:00 · Nathan 20.4% · guest 79.6%15:00 · Nathan 19.4% · guest 80.6%15:00 · Nathan 19.4% · guest 80.6%18:00 · Nathan 86.4% · guest 13.6%18:00 · Nathan 86.4% · guest 13.6%
Sharpest disagreement ▶ 10:14 Candid Admission on Unit Economics Uncertainty

Brett pushes back against rigid unit economics modeling by openly admitting he does not track exact acquisition costs and relies on general rules of thumb.

 Hardest push from Nathan ▶ 11:53 Host Recommends Higher Upfront Pricing

Nathan directly challenges Brett's flat monthly pricing structure, arguing that charging $500-$600 upfront would weed out uncommitted users and reduce churn.

 Biggest teaching moment ▶ 7:49 Explaining Structural Churn in E-Commerce SaaS

Brett educates Nathan on why their churn remains near 8% monthly, explaining that small online store shutdowns account for most cancellations rather than product dissatisfaction.

 Nathan holds their own ▶ 11:23 Instant Customer Lifetime Calculation

Nathan demonstrates SaaS financial mastery by taking the 8% churn metric, computing a 12.5-month average lifespan on the spot, and modeling the corresponding customer lifetime value.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Guest Welcome and Early LeadDyno Milestones 4212 Nathan opens by checking Brett's early timeline and clarifying the distinction between initial MRR and customer counts. Brett collaboratively details the initial three cofounders and bootstrapping history.
Product Value Proposition, Pricing, and Acquisition Channels 6112 Nathan quickly runs the mental math on ARPU and customer volume to calculate monthly run rate and ARR. Brett outlines LeadDyno's product differentiation and acquisition channels via app store integrations.
Host Note on Podcast Scheduling and Early Access 5314 Nathan presses Brett on competitor differentiation and drills into monthly logo churn numbers. Brett transparently acknowledges high single-digit churn driven by customer business mortality in e-commerce.
Sponsor Message: Gusto Payroll and HR Platform 7214 Following the sponsor break, Nathan computes customer lifetime from the 8% monthly churn rate and challenges Brett to test upfront annual pricing. Brett admits they have only tested monthly pricing and shares past freemium lessons.
Team Distribution and Philosophy on Bootstrapping 4212 Nathan explores the remote team structure and conducts the Famous Five questionnaire, pushing slightly on whether dedicated live chat headcount is worth the payroll cost.
Lessons from Past Startup Mistakes and Delayed Exits 4312 Brett reflects candidly on losing $300k on his first business before selling at a loss. Nathan validates the painful lesson of knowing when to exit a stagnant business early.

Statements from this episode (10)

Assertion Not checkable as stated
LeadDyno exceeds $1 million in annual revenue
“We're above seven figures now in terms of annual revenue numbers.”
Brett Owens Dec 8, 2018 ▶ 2:49
Assertion Not checkable as stated
LeadDyno serves over 2,400 customers
“We're over 2400 on the customer side of Leaddyno.”
Brett Owens Dec 8, 2018 ▶ 2:56
Disclosure
LeadDyno's average customer pays under $100 per month
“Our pricing is between it starts at 29 a month and then it goes up to two 49 a month, actually up to three 49. But we're under a hundred dollars a month in terms of what they're paying.”
Brett Owens Dec 8, 2018 ▶ 4:09
Assertion Not checkable as stated
LeadDyno grew revenue by 30% year-over-year in 2017
“Growth rate, I believe we grew about 30% year over year last year. So 20 sets, 20 17 over 20 16.”
Brett Owens Dec 8, 2018 ▶ 4:40
Assertion Not checkable as stated
LeadDyno experiences roughly 8% monthly logo churn
“So churn is in the high single digits. Our churn is actually, I would say high for a SaaS company. Monthly? Yeah, monthly. Okay, so call it like eight percent logo churn per month, something like that? Yeah, I would say that's I would say that's fair.”
Brett Owens Dec 8, 2018 ▶ 7:37
Insight
LeadDyno's high churn is driven by customers closing their e-commerce stores
“People sign up and then they leave and you feel bad and you find that the reason that they left is oftentimes they shut down their online store.”
Brett Owens Dec 8, 2018 ▶ 8:09
Disclosure
LeadDyno has never tested annual contracts or charged setup fees
“We've also never tested doing something yearly. We've always been flat monthly and no setup costs either, where I know some of the big networks and that's always been a drawing point for us.”
Brett Owens Dec 8, 2018 ▶ 11:59
Insight
LeadDyno scrapped freemium and $19 tiers for attracting non-serious customers
“We did have a failed experiment with a freemium type model where we offered free versions, and that was a complete mess because the type of customer you get free is not the type where even, even we found 19 to be maybe didn't have as many serious people as we …”
Brett Owens Dec 8, 2018 ▶ 12:36
Assertion Not checkable as stated
Half of LeadDyno signups interact with live chat before converting
“I would say I know you love the numbers, I would say probably one in two people who sign up for our, an account with us, Hit us up on live chat before.”
Brett Owens Dec 8, 2018 ▶ 16:36
Assertion Not checkable as stated
Owens recovered under 30 cents on the dollar for $300k startup loan
“The company still owed me personally on, on the balance sheet, like, 300,000 dollars, because I ended up being the angel investor, and it wasn't pretty, it wasn't like I had the money. It was like a forwarding off a credit card on the company balance sheet, an…”
Brett Owens Dec 8, 2018 ▶ 17:45
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