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Jul 12, 2020 · 16m · top-founders

MediaFly To Acquire More, $20m in ARR, Burning $600k/mo, $28m Raised

Carson Conant · 9m spoken Nathan Latka · 4m spoken Eric Yuan · 4s spoken Vivek Bhaskaran · 2s spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Mediafly CEO Carson Conant discusses the company's growth toward a $20 million ARR run rate, detailing its strategic acquisition of iPresent, enterprise retention economics, and upcoming Series C funding round. The interview highlights Mediafly's land-and-expand go-to-market strategy and disciplined M&A playbook to outcompete sales enablement rivals.

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 34.4% of the talking time here. How this is scored →

Nathan as informed peer 4.7 Guest teaching 1.3 Guest disagreement 0.8 Nathan pushing back 2.2
05100:0010:000:12–3:41 · Nathan as informed peer 3/10 Latka Subscription Promotion and Archive Highlights The segment begins with Nathan's promotional monologue and archive clips before introducing Carson Conant. Carson outlines Mediafly's acquisition of UK-based iPresent to introduce a self-serve freemium model to compete against Showpad and Seismic.3:41–7:22 · Nathan as informed peer 7/10 Shifting ACV, Freemium Adoption, and Customer Expansion Nathan drills into Carson's lowering ACV and the split between organic growth and acquisition-driven customer adds. Nathan actively models hypothetical M&A debt financing structures using banking partners like CIBC.7:23–10:35 · Nathan as informed peer 7/10 Team Scaling, Monthly Burn, and Series C Plans Nathan presses Carson by citing exact figures from their prior interview regarding burn rate, team headcount, and monthly revenue. Carson outlines plans for a $30M to $50M Series C round alongside cap table secondary cleanups.10:35–12:42 · Nathan as informed peer 7/10 Enterprise Retention Performance and Net Expansion Analysis Nathan tests Carson's retention metrics against previous historical interview data to verify reporting consistency. Carson details their 98% gross retention and 110% net expansion dynamics.12:43–15:36 · Nathan as informed peer 4/10 Post-Acquisition Team Structure and Sales Organization Nathan queries the exact team composition between engineering and quota-carrying sales reps before running through the standard Famous Five rapid-fire questions.15:36–16:03 · Nathan as informed peer 0/10 Episode Summary, Financial Highlights, and Conclusion Nathan delivers a rapid solo recap of Mediafly's financial metrics, headcounts, burn, and growth trajectory. Monologue scoring rules apply with zero host-guest interactive scores.0:12–3:41 · Guest teaching 1/10 Latka Subscription Promotion and Archive Highlights The segment begins with Nathan's promotional monologue and archive clips before introducing Carson Conant. Carson outlines Mediafly's acquisition of UK-based iPresent to introduce a self-serve freemium model to compete against Showpad and Seismic.3:41–7:22 · Guest teaching 2/10 Shifting ACV, Freemium Adoption, and Customer Expansion Nathan drills into Carson's lowering ACV and the split between organic growth and acquisition-driven customer adds. Nathan actively models hypothetical M&A debt financing structures using banking partners like CIBC.7:23–10:35 · Guest teaching 2/10 Team Scaling, Monthly Burn, and Series C Plans Nathan presses Carson by citing exact figures from their prior interview regarding burn rate, team headcount, and monthly revenue. Carson outlines plans for a $30M to $50M Series C round alongside cap table secondary cleanups.10:35–12:42 · Guest teaching 2/10 Enterprise Retention Performance and Net Expansion Analysis Nathan tests Carson's retention metrics against previous historical interview data to verify reporting consistency. Carson details their 98% gross retention and 110% net expansion dynamics.12:43–15:36 · Guest teaching 1/10 Post-Acquisition Team Structure and Sales Organization Nathan queries the exact team composition between engineering and quota-carrying sales reps before running through the standard Famous Five rapid-fire questions.15:36–16:03 · Guest teaching 0/10 Episode Summary, Financial Highlights, and Conclusion Nathan delivers a rapid solo recap of Mediafly's financial metrics, headcounts, burn, and growth trajectory. Monologue scoring rules apply with zero host-guest interactive scores.0:12–3:41 · Guest disagreement 1/10 Latka Subscription Promotion and Archive Highlights The segment begins with Nathan's promotional monologue and archive clips before introducing Carson Conant. Carson outlines Mediafly's acquisition of UK-based iPresent to introduce a self-serve freemium model to compete against Showpad and Seismic.3:41–7:22 · Guest disagreement 1/10 Shifting ACV, Freemium Adoption, and Customer Expansion Nathan drills into Carson's lowering ACV and the split between organic growth and acquisition-driven customer adds. Nathan actively models hypothetical M&A debt financing structures using banking partners like CIBC.7:23–10:35 · Guest disagreement 1/10 Team Scaling, Monthly Burn, and Series C Plans Nathan presses Carson by citing exact figures from their prior interview regarding burn rate, team headcount, and monthly revenue. Carson outlines plans for a $30M to $50M Series C round alongside cap table secondary cleanups.10:35–12:42 · Guest disagreement 1/10 Enterprise Retention Performance and Net Expansion Analysis Nathan tests Carson's retention metrics against previous historical interview data to verify reporting consistency. Carson details their 98% gross retention and 110% net expansion dynamics.12:43–15:36 · Guest disagreement 1/10 Post-Acquisition Team Structure and Sales Organization Nathan queries the exact team composition between engineering and quota-carrying sales reps before running through the standard Famous Five rapid-fire questions.15:36–16:03 · Guest disagreement 0/10 Episode Summary, Financial Highlights, and Conclusion Nathan delivers a rapid solo recap of Mediafly's financial metrics, headcounts, burn, and growth trajectory. Monologue scoring rules apply with zero host-guest interactive scores.0:12–3:41 · Nathan pushing back 1/10 Latka Subscription Promotion and Archive Highlights The segment begins with Nathan's promotional monologue and archive clips before introducing Carson Conant. Carson outlines Mediafly's acquisition of UK-based iPresent to introduce a self-serve freemium model to compete against Showpad and Seismic.3:41–7:22 · Nathan pushing back 3/10 Shifting ACV, Freemium Adoption, and Customer Expansion Nathan drills into Carson's lowering ACV and the split between organic growth and acquisition-driven customer adds. Nathan actively models hypothetical M&A debt financing structures using banking partners like CIBC.7:23–10:35 · Nathan pushing back 4/10 Team Scaling, Monthly Burn, and Series C Plans Nathan presses Carson by citing exact figures from their prior interview regarding burn rate, team headcount, and monthly revenue. Carson outlines plans for a $30M to $50M Series C round alongside cap table secondary cleanups.10:35–12:42 · Nathan pushing back 3/10 Enterprise Retention Performance and Net Expansion Analysis Nathan tests Carson's retention metrics against previous historical interview data to verify reporting consistency. Carson details their 98% gross retention and 110% net expansion dynamics.12:43–15:36 · Nathan pushing back 2/10 Post-Acquisition Team Structure and Sales Organization Nathan queries the exact team composition between engineering and quota-carrying sales reps before running through the standard Famous Five rapid-fire questions.15:36–16:03 · Nathan pushing back 0/10 Episode Summary, Financial Highlights, and Conclusion Nathan delivers a rapid solo recap of Mediafly's financial metrics, headcounts, burn, and growth trajectory. Monologue scoring rules apply with zero host-guest interactive scores.

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

0:00 · Nathan 62.4% · guest 37.6%0:00 · Nathan 62.4% · guest 37.6%3:00 · Nathan 18.8% · guest 81.2%3:00 · Nathan 18.8% · guest 81.2%6:00 · Nathan 35.2% · guest 64.8%6:00 · Nathan 35.2% · guest 64.8%9:00 · Nathan 32.5% · guest 67.5%9:00 · Nathan 32.5% · guest 67.5%12:00 · Nathan 13.4% · guest 86.6%12:00 · Nathan 13.4% · guest 86.6%15:00 · Nathan 63.7% · guest 36.3%15:00 · Nathan 63.7% · guest 36.3%
Sharpest disagreement ▶ 2:30 Carson defends the self-serve model against enterprise skepticism

Carson firmly rejects the idea that sales enablement should only be sold via lengthy 18-month enterprise cycles, arguing a freemium tier beats incumbent rivals.

 Hardest push from Nathan ▶ 6:09 Nathan pushes on debt structure and equity requirements

Nathan directly presses Carson on how much equity is required versus debt leverage when acquiring SaaS targets.

 Biggest teaching moment ▶ 6:38 Carson details M&A financing mechanics

Carson breaks down how Mediafly structures deals using a one-third cash, one-third stock, and one-third earn-out framework leveraged with bank debt.

 Nathan holds their own ▶ 11:31 Nathan cross-checks Carson's historical retention figures

Nathan demonstrates mastery of Carson's metrics by quoting his exact gross and net retention rates from months prior to verify consistency.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Latka Subscription Promotion and Archive Highlights 3111 The segment begins with Nathan's promotional monologue and archive clips before introducing Carson Conant. Carson outlines Mediafly's acquisition of UK-based iPresent to introduce a self-serve freemium model to compete against Showpad and Seismic.
Shifting ACV, Freemium Adoption, and Customer Expansion 7213 Nathan drills into Carson's lowering ACV and the split between organic growth and acquisition-driven customer adds. Nathan actively models hypothetical M&A debt financing structures using banking partners like CIBC.
Team Scaling, Monthly Burn, and Series C Plans 7214 Nathan presses Carson by citing exact figures from their prior interview regarding burn rate, team headcount, and monthly revenue. Carson outlines plans for a $30M to $50M Series C round alongside cap table secondary cleanups.
Enterprise Retention Performance and Net Expansion Analysis 7213 Nathan tests Carson's retention metrics against previous historical interview data to verify reporting consistency. Carson details their 98% gross retention and 110% net expansion dynamics.
Post-Acquisition Team Structure and Sales Organization 4112 Nathan queries the exact team composition between engineering and quota-carrying sales reps before running through the standard Famous Five rapid-fire questions.
Episode Summary, Financial Highlights, and Conclusion 0000 Nathan delivers a rapid solo recap of Mediafly's financial metrics, headcounts, burn, and growth trajectory. Monologue scoring rules apply with zero host-guest interactive scores.

Statements from this episode (18)

Disclosure
Mediafly Acquires iPresent to Add Self-Serve Freemium Model
“So we acquired a company called iPresent UK based company, UK and here, but it's a, it gives us a self-serve kind of a premium model that is pretty unique in this space.”
Carson Conant Jul 12, 2020 ▶ 2:16
Assertion Not checkable as stated
Mediafly Cuts Sales Cycle to Under 30 Days
“So you know, they'll grow over the next, you know, 1824 months, but we can, you know, we can close new customers in less than 30 days now, whereas historically it took, you know, several months.”
Carson Conant Jul 12, 2020 ▶ 4:06
Disclosure
Mediafly Counts 260 Customers in Mid-2020
“I think it's, 260 customers right now.”
Carson Conant Jul 12, 2020 ▶ 4:17
Disclosure
Two-Thirds of Mediafly's Recent Customer Growth Was M&A
“Probably about half the, let's see, probably about a third of that growth since the last time you and I talked was organic. The other two thirds came from this acquisition.”
Carson Conant Jul 12, 2020 ▶ 4:53
Disclosure
Mediafly Used Cash and Debt to Acquire iPresent
“We did end up putting some cash up. I don't think I'm allowed to say what it was, but this, what it did include cash as well as debt on our side.”
Carson Conant Jul 12, 2020 ▶ 5:47
Disclosure
Mediafly Can Raise Up to 1x ARR in Debt
“So the combination of, you know, CIBC and then other folks, I think we can get to about one times ARR if we wanted to.”
Carson Conant Jul 12, 2020 ▶ 6:38
Disclosure
Mediafly Targets a One-Third Cash, Stock, and Earn-Out M&A Structure
“And I think the model we've been looking at is kind of a one-third, one-third, one-third, where it's maybe a one-third in cash upfront, one-third in stock and then one-third in, in in kind of earn-out notes.”
Carson Conant Jul 12, 2020 ▶ 6:51
Assertion Not checkable as stated
Mediafly Headcount Reaches Around 120 Employees
“So we're now, we just, we added 22, kept everybody so I think we're a hundred and 20 now, I want to say.”
Carson Conant Jul 12, 2020 ▶ 7:26
Prediction Partly held up
Mediafly Expects to Close Series C by Early 2021
“We think we'll close this, our series C somewhere end of this calendar year first couple months of the next.”
Carson Conant Jul 12, 2020 ▶ 8:07
Disclosure
Mediafly Plans Up to Two Acquisitions Next Fiscal Year
“My guess is we'll do another acquisition next fiscal year. Potentially two.”
Carson Conant Jul 12, 2020 ▶ 9:35
Prediction Not checkable as stated
Mediafly CEO expects company to close the year just under $20M ARR
“I think we'll close the year about a little shy of twenty million in ARR.”
Carson Conant Jul 12, 2020 ▶ 10:22
Assertion Not checkable as stated
Mediafly Gross Revenue Retention Was 98% Last Year
“I think our gross retention last year was 98%.”
Carson Conant Jul 12, 2020 ▶ 10:44
Assertion Not checkable as stated
Mediafly Lost Only One Customer Logo Last Year
“I think we only lost one logo all of last year.”
Carson Conant Jul 12, 2020 ▶ 10:56
Prediction Not checkable as stated
Mediafly Gross Retention Will Reach 92% to 95% This Year
“This year, I guess it's probably going to be in that kind of 92 to 95% range would be my guess.”
Carson Conant Jul 12, 2020 ▶ 11:11
Assertion Not checkable as stated
Mediafly Net Revenue Retention Was About 110% Last Year
“I want to say our net retention last year was, you know, about a 110%, something like that.”
Carson Conant Jul 12, 2020 ▶ 11:28
Assertion Not checkable as stated
Mediafly CAC Payback Period is in the 12-Month Range
“I think the payback period will be you know, will be similar. I think it's probably in that 12 month range”
Carson Conant Jul 12, 2020 ▶ 12:00
Opinion
iPresent Acquisition Enables Mediafly to Win Against Showpad Faster
“Part of what this acquisition does for us is allow us to go, we can go target companies that are actively looking at Showpad and, you know, win them quicker.”
Carson Conant Jul 12, 2020 ▶ 14:00
What-if
Mediafly CEO Regrets Not Investing in Sales and Marketing Earlier
“Invest earlier in sales and marketing. You know, I'm a product. I'm a product CEO. I'm a product lover. You know, I love the product. I'm a programmer by background. I would have invested earlier in marketing and sales.”
Carson Conant Jul 12, 2020 ▶ 15:26
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