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Aug 6, 2019 · 15m · top-founders

1473 How to Raise $500k From Early Channel Partners To Break $20k/mo in MRR

Nathan Latka · 7m spoken Brennan Dunn · 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 RightMessage co-founder Brennan Dunn to discuss how his website personalization platform raised $500,000 from strategic channel partners and scaled past $20,000 in monthly recurring revenue. Brennan breaks down his transition from freelancing education to SaaS, key customer metrics, capital-efficient fundraising, and team operations.

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 51.4% of the talking time here. How this is scored →

Nathan as informed peer 4.4 Guest teaching 2.6 Guest disagreement 1.2 Nathan pushing back 3.2
05100:0010:000:00–2:13 · Nathan as informed peer 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Introductory monologue and promotional book read by Nathan Latka with audio clips from the podcast catalog.2:14–4:19 · Nathan as informed peer 5/10 Brennan Dunn's Background from Freelancing to SaaS Nathan posits a common agency-to-SaaS trajectory, but Brennan clarifies his specific path through course creation and info products.4:20–7:56 · Nathan as informed peer 6/10 RightMessage Product Mechanics, Metrics, and Strategic Funding Nathan drills into the unit economics, questioning how direct sales calls make sense for a $144 ARPU product, which Brennan justifies as unscalable customer research.8:00–11:55 · Nathan as informed peer 5/10 Gusto HR and Payroll Sponsorship Following the mid-roll ad read, Nathan clarifies team size and explores the operational complexity of infinite personalization funnels.11:56–15:01 · Nathan as informed peer 6/10 Fundraising Strategy, Valuation Cap, and Profitability Goals Nathan probes the SAFE valuation cap and challenges the idea of maintaining a pure bootstrapper mindset after taking outside capital.0:00–2:13 · Guest teaching 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Introductory monologue and promotional book read by Nathan Latka with audio clips from the podcast catalog.2:14–4:19 · Guest teaching 4/10 Brennan Dunn's Background from Freelancing to SaaS Nathan posits a common agency-to-SaaS trajectory, but Brennan clarifies his specific path through course creation and info products.4:20–7:56 · Guest teaching 3/10 RightMessage Product Mechanics, Metrics, and Strategic Funding Nathan drills into the unit economics, questioning how direct sales calls make sense for a $144 ARPU product, which Brennan justifies as unscalable customer research.8:00–11:55 · Guest teaching 3/10 Gusto HR and Payroll Sponsorship Following the mid-roll ad read, Nathan clarifies team size and explores the operational complexity of infinite personalization funnels.11:56–15:01 · Guest teaching 3/10 Fundraising Strategy, Valuation Cap, and Profitability Goals Nathan probes the SAFE valuation cap and challenges the idea of maintaining a pure bootstrapper mindset after taking outside capital.0:00–2:13 · Guest disagreement 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Introductory monologue and promotional book read by Nathan Latka with audio clips from the podcast catalog.2:14–4:19 · Guest disagreement 1/10 Brennan Dunn's Background from Freelancing to SaaS Nathan posits a common agency-to-SaaS trajectory, but Brennan clarifies his specific path through course creation and info products.4:20–7:56 · Guest disagreement 2/10 RightMessage Product Mechanics, Metrics, and Strategic Funding Nathan drills into the unit economics, questioning how direct sales calls make sense for a $144 ARPU product, which Brennan justifies as unscalable customer research.8:00–11:55 · Guest disagreement 1/10 Gusto HR and Payroll Sponsorship Following the mid-roll ad read, Nathan clarifies team size and explores the operational complexity of infinite personalization funnels.11:56–15:01 · Guest disagreement 2/10 Fundraising Strategy, Valuation Cap, and Profitability Goals Nathan probes the SAFE valuation cap and challenges the idea of maintaining a pure bootstrapper mindset after taking outside capital.0:00–2:13 · Nathan pushing back 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Introductory monologue and promotional book read by Nathan Latka with audio clips from the podcast catalog.2:14–4:19 · Nathan pushing back 3/10 Brennan Dunn's Background from Freelancing to SaaS Nathan posits a common agency-to-SaaS trajectory, but Brennan clarifies his specific path through course creation and info products.4:20–7:56 · Nathan pushing back 5/10 RightMessage Product Mechanics, Metrics, and Strategic Funding Nathan drills into the unit economics, questioning how direct sales calls make sense for a $144 ARPU product, which Brennan justifies as unscalable customer research.8:00–11:55 · Nathan pushing back 4/10 Gusto HR and Payroll Sponsorship Following the mid-roll ad read, Nathan clarifies team size and explores the operational complexity of infinite personalization funnels.11:56–15:01 · Nathan pushing back 4/10 Fundraising Strategy, Valuation Cap, and Profitability Goals Nathan probes the SAFE valuation cap and challenges the idea of maintaining a pure bootstrapper mindset after taking outside capital.

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

0:00 · Nathan 85.1% · guest 14.9%0:00 · Nathan 85.1% · guest 14.9%3:00 · Nathan 35.6% · guest 64.4%3:00 · Nathan 35.6% · guest 64.4%6:00 · Nathan 54.9% · guest 45.1%6:00 · Nathan 54.9% · guest 45.1%9:00 · Nathan 40.5% · guest 59.5%9:00 · Nathan 40.5% · guest 59.5%12:00 · Nathan 27.5% · guest 72.5%12:00 · Nathan 27.5% · guest 72.5%15:00 · Nathan 93.8% · guest 6.2%15:00 · Nathan 93.8% · guest 6.2%
Sharpest disagreement ▶ 6:00 Brennan defends doing unscalable direct sales calls

Brennan pushes back on the premise that sales calls must immediately scale, asserting the immediate learning value outweighs the short-term cost.

 Hardest push from Nathan ▶ 5:54 Nathan challenges sales touch on low ARPU tier

Nathan directly challenges the sustainability of putting high-touch human sales efforts behind a $150/month product.

 Biggest teaching moment ▶ 2:43 Brennan corrects Nathan's assumption about agency history

Brennan politely dismantles Nathan's agency-to-SaaS narrative by explaining his actual sequence of agency exit, software exit, and info product sales.

 Nathan holds their own ▶ 12:48 Nathan emphasizes how raising capital changes corporate dynamics

Nathan demonstrates venture knowledge by noting that taking even a small amount of outside capital structurally shifts company incentives regardless of founder intent.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Book Promotion: How to Be a Capitalist Without Any Capital 0000 Introductory monologue and promotional book read by Nathan Latka with audio clips from the podcast catalog.
Brennan Dunn's Background from Freelancing to SaaS 5413 Nathan posits a common agency-to-SaaS trajectory, but Brennan clarifies his specific path through course creation and info products.
RightMessage Product Mechanics, Metrics, and Strategic Funding 6325 Nathan drills into the unit economics, questioning how direct sales calls make sense for a $144 ARPU product, which Brennan justifies as unscalable customer research.
Gusto HR and Payroll Sponsorship 5314 Following the mid-roll ad read, Nathan clarifies team size and explores the operational complexity of infinite personalization funnels.
Fundraising Strategy, Valuation Cap, and Profitability Goals 6324 Nathan probes the SAFE valuation cap and challenges the idea of maintaining a pure bootstrapper mindset after taking outside capital.

Statements from this episode (11)

Disclosure
Brennan Dunn sold software startup Planscope for six figures in 2016
“It was a, I mean, it was a six figure exit. It wasn't huge, right? Our plans never did that well.”
Brennan Dunn Aug 6, 2019 ▶ 3:10
Assertion Not checkable as stated
RightMessage's ARPU is $144 per month
“Average ARPU is 144 at the moment.”
Brennan Dunn Aug 6, 2019 ▶ 5:12
Assertion Not checkable as stated
RightMessage reached $20k MRR three and a half months after launch
“Yeah, we launched in January. We're at, we're just about 20,000 MRR. So in about Three and a half months.”
Brennan Dunn Aug 6, 2019 ▶ 5:23
Assertion Not checkable as stated
RightMessage's revenue is growing 30% to 40% month-over-month
“We're growing 30, 40% a month now and happy with it.”
Brennan Dunn Aug 6, 2019 ▶ 5:32
Assertion Not checkable as stated
RightMessage's monthly user churn is about 5%
“Churn right now is about five percent.”
Brennan Dunn Aug 6, 2019 ▶ 6:27
Disclosure
RightMessage raised $500k from integration partners including ConvertKit and Leadpages
“No, we raised half a million. So we raised from early customers along with, Some of the companies we integrate with, like ConvertKit, Leadpages, Drip, and so on.”
Brennan Dunn Aug 6, 2019 ▶ 7:16
Disclosure
Brennan Dunn owns 50% of RightMessage with co-founder Shai
“I know I own half the company. I have a co-founder who's the technical co-founder, Shai.”
Brennan Dunn Aug 6, 2019 ▶ 9:48
Assertion Not checkable as stated
RightMessage raised its early round in one week without a pitch deck
“It was back in October and it only took, it took about a week. No pitch checker. They were all friends of mine, so I just really emailed them and did it that way.”
Brennan Dunn Aug 6, 2019 ▶ 12:18
Disclosure
RightMessage plans to stay profitable and avoid a Series A round
“Profitable out of the gate. So we're not looking to jump from the different to series A or anything like that.”
Brennan Dunn Aug 6, 2019 ▶ 12:35
Assertion Not checkable as stated
Teachable founder Ankur Nagpal convinced RightMessage to raise venture capital
“We were going to bootstrap, but our first customer was Teachable, and Anker reached out saying, I want the product faster. Can you raise some money and build a team on it?”
Brennan Dunn Aug 6, 2019 ▶ 13:16
What-if
Dunn: Wishes he had stayed in college instead of dropping out
“Probably would have stayed in college. I dropped out, ah, kind of wish I would have probably stuck with it a few more years, but yeah.”
Brennan Dunn Aug 6, 2019 ▶ 14:55
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