StarZero All shows Try the podcast clipper →

Oct 1, 2019 · 17m · top-founders

1529 Will This Company Ever Scale Past $6k/mo?

Rishikesh Kale · 8m spoken
0:00 / 0:00

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

Entrepreneur Rishikesh Kale discusses the monetization, organic growth tactics, and churn metrics of his email productivity SaaS Mailtag while addressing co-founder restructuring and valuation debates. The conversation examines whether the startup can scale past its $4,500 monthly revenue plateau amid entrenched market competition.

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 43.2% of the talking time here. How this is scored →

Nathan as informed peer 6.2 Guest teaching 1.3 Guest disagreement 2.2 Nathan pushing back 5.3
05100:0010:001:04–4:24 · Nathan as informed peer 5/10 Mailtag Product Capabilities and Team Structure Nathan clarifies Rishikesh's role as CTO and team split between India and Phoenix. When Rishikesh starts recounting older company history, Nathan interrupts to redirect focus back to the current revenue-generating business.4:24–7:58 · Nathan as informed peer 6/10 Pricing Strategy, Seed Capital, and Current Revenue Nathan probes unit economics, customer numbers, and churn metrics. When Nathan calculates baseline MRR at $3,000, Rishikesh corrects him with their tiered plan pricing totaling $4,500.7:58–11:00 · Nathan as informed peer 8/10 Fundraising Discussions and Co-Founder Dynamics Nathan reveals insider knowledge that co-founder Alex Edson is moving on to SocialCo.io. Nathan repeatedly challenges Rishikesh on how they can raise capital when the CEO has checked out.11:00–13:15 · Nathan as informed peer 8/10 Market Saturation and Competitive Differentiation Nathan benchmarks Mailtag against Boomerang's $600k MRR and Yesware. When Rishikesh asserts users are abandoning competitors for Mailtag and claims every space is hyper-competitive, Nathan directly rejects both claims as factually unfounded.13:16–15:26 · Nathan as informed peer 7/10 Company Valuation Debate and Net Expansion Nathan rejects multiple non-answers about valuation, demanding an exact figure. Once Rishikesh provides a $1M to $2M estimate, Nathan immediately points out it represents an aggressive 20x revenue multiple on $50k ARR.15:26–16:33 · Nathan as informed peer 3/10 The Famous Five Rapid-Fire Questions Nathan moves through standard Famous Five rapid-fire questions covering favorite business books, tools, and personal background smoothly.1:04–4:24 · Guest teaching 1/10 Mailtag Product Capabilities and Team Structure Nathan clarifies Rishikesh's role as CTO and team split between India and Phoenix. When Rishikesh starts recounting older company history, Nathan interrupts to redirect focus back to the current revenue-generating business.4:24–7:58 · Guest teaching 3/10 Pricing Strategy, Seed Capital, and Current Revenue Nathan probes unit economics, customer numbers, and churn metrics. When Nathan calculates baseline MRR at $3,000, Rishikesh corrects him with their tiered plan pricing totaling $4,500.7:58–11:00 · Guest teaching 1/10 Fundraising Discussions and Co-Founder Dynamics Nathan reveals insider knowledge that co-founder Alex Edson is moving on to SocialCo.io. Nathan repeatedly challenges Rishikesh on how they can raise capital when the CEO has checked out.11:00–13:15 · Guest teaching 1/10 Market Saturation and Competitive Differentiation Nathan benchmarks Mailtag against Boomerang's $600k MRR and Yesware. When Rishikesh asserts users are abandoning competitors for Mailtag and claims every space is hyper-competitive, Nathan directly rejects both claims as factually unfounded.13:16–15:26 · Guest teaching 1/10 Company Valuation Debate and Net Expansion Nathan rejects multiple non-answers about valuation, demanding an exact figure. Once Rishikesh provides a $1M to $2M estimate, Nathan immediately points out it represents an aggressive 20x revenue multiple on $50k ARR.15:26–16:33 · Guest teaching 1/10 The Famous Five Rapid-Fire Questions Nathan moves through standard Famous Five rapid-fire questions covering favorite business books, tools, and personal background smoothly.1:04–4:24 · Guest disagreement 1/10 Mailtag Product Capabilities and Team Structure Nathan clarifies Rishikesh's role as CTO and team split between India and Phoenix. When Rishikesh starts recounting older company history, Nathan interrupts to redirect focus back to the current revenue-generating business.4:24–7:58 · Guest disagreement 1/10 Pricing Strategy, Seed Capital, and Current Revenue Nathan probes unit economics, customer numbers, and churn metrics. When Nathan calculates baseline MRR at $3,000, Rishikesh corrects him with their tiered plan pricing totaling $4,500.7:58–11:00 · Guest disagreement 3/10 Fundraising Discussions and Co-Founder Dynamics Nathan reveals insider knowledge that co-founder Alex Edson is moving on to SocialCo.io. Nathan repeatedly challenges Rishikesh on how they can raise capital when the CEO has checked out.11:00–13:15 · Guest disagreement 5/10 Market Saturation and Competitive Differentiation Nathan benchmarks Mailtag against Boomerang's $600k MRR and Yesware. When Rishikesh asserts users are abandoning competitors for Mailtag and claims every space is hyper-competitive, Nathan directly rejects both claims as factually unfounded.13:16–15:26 · Guest disagreement 3/10 Company Valuation Debate and Net Expansion Nathan rejects multiple non-answers about valuation, demanding an exact figure. Once Rishikesh provides a $1M to $2M estimate, Nathan immediately points out it represents an aggressive 20x revenue multiple on $50k ARR.15:26–16:33 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions Nathan moves through standard Famous Five rapid-fire questions covering favorite business books, tools, and personal background smoothly.1:04–4:24 · Nathan pushing back 4/10 Mailtag Product Capabilities and Team Structure Nathan clarifies Rishikesh's role as CTO and team split between India and Phoenix. When Rishikesh starts recounting older company history, Nathan interrupts to redirect focus back to the current revenue-generating business.4:24–7:58 · Nathan pushing back 3/10 Pricing Strategy, Seed Capital, and Current Revenue Nathan probes unit economics, customer numbers, and churn metrics. When Nathan calculates baseline MRR at $3,000, Rishikesh corrects him with their tiered plan pricing totaling $4,500.7:58–11:00 · Nathan pushing back 8/10 Fundraising Discussions and Co-Founder Dynamics Nathan reveals insider knowledge that co-founder Alex Edson is moving on to SocialCo.io. Nathan repeatedly challenges Rishikesh on how they can raise capital when the CEO has checked out.11:00–13:15 · Nathan pushing back 8/10 Market Saturation and Competitive Differentiation Nathan benchmarks Mailtag against Boomerang's $600k MRR and Yesware. When Rishikesh asserts users are abandoning competitors for Mailtag and claims every space is hyper-competitive, Nathan directly rejects both claims as factually unfounded.13:16–15:26 · Nathan pushing back 8/10 Company Valuation Debate and Net Expansion Nathan rejects multiple non-answers about valuation, demanding an exact figure. Once Rishikesh provides a $1M to $2M estimate, Nathan immediately points out it represents an aggressive 20x revenue multiple on $50k ARR.15:26–16:33 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions Nathan moves through standard Famous Five rapid-fire questions covering favorite business books, tools, and personal background smoothly.

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

0:00 · Nathan 50.5% · guest 49.5%0:00 · Nathan 50.5% · guest 49.5%3:00 · Nathan 24.6% · guest 75.4%3:00 · Nathan 24.6% · guest 75.4%6:00 · Nathan 25% · guest 75%6:00 · Nathan 25% · guest 75%9:00 · Nathan 54.2% · guest 45.8%9:00 · Nathan 54.2% · guest 45.8%12:00 · Nathan 53% · guest 47%12:00 · Nathan 53% · guest 47%15:00 · Nathan 58.4% · guest 41.6%15:00 · Nathan 58.4% · guest 41.6%
Sharpest disagreement ▶ 12:49 Guest defends crowded market position

Rishikesh pushes back against Nathan's market saturation critique by arguing that every industry is hyper-competitive.

 Hardest push from Nathan ▶ 10:09 Host confronts guest with co-founder departure

Nathan refuses vague fundraising talking points by directly pointing out that the CEO is launching a separate venture.

 Biggest teaching moment ▶ 5:20 Guest corrects MRR calculation

Rishikesh corrects Nathan's $3,000 revenue estimate by explaining their multi-tier pricing structure yields $4,500 monthly.

 Nathan holds their own ▶ 11:37 Host cites competitor data to dispute market superiority

Nathan cites Boomerang's $600k/mo revenue figure to counter Rishikesh's claim that Mailtag offers superior market traction.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Mailtag Product Capabilities and Team Structure 5114 Nathan clarifies Rishikesh's role as CTO and team split between India and Phoenix. When Rishikesh starts recounting older company history, Nathan interrupts to redirect focus back to the current revenue-generating business.
Pricing Strategy, Seed Capital, and Current Revenue 6313 Nathan probes unit economics, customer numbers, and churn metrics. When Nathan calculates baseline MRR at $3,000, Rishikesh corrects him with their tiered plan pricing totaling $4,500.
Fundraising Discussions and Co-Founder Dynamics 8138 Nathan reveals insider knowledge that co-founder Alex Edson is moving on to SocialCo.io. Nathan repeatedly challenges Rishikesh on how they can raise capital when the CEO has checked out.
Market Saturation and Competitive Differentiation 8158 Nathan benchmarks Mailtag against Boomerang's $600k MRR and Yesware. When Rishikesh asserts users are abandoning competitors for Mailtag and claims every space is hyper-competitive, Nathan directly rejects both claims as factually unfounded.
Company Valuation Debate and Net Expansion 7138 Nathan rejects multiple non-answers about valuation, demanding an exact figure. Once Rishikesh provides a $1M to $2M estimate, Nathan immediately points out it represents an aggressive 20x revenue multiple on $50k ARR.
The Famous Five Rapid-Fire Questions 3101 Nathan moves through standard Famous Five rapid-fire questions covering favorite business books, tools, and personal background smoothly.

Statements from this episode (11)

Assertion Not checkable as stated
Mailtag has eight team members split between India and Arizona
“Now we have a team of a eight people with us working on this product. Most of my team is split between Pune, India and Phoenix Arizona.”
Rishikesh Kale Oct 1, 2019 ▶ 2:37
Disclosure
Kale: Mailtag bootstrapped with $250K in founder capital
“We bootstrap it with a seed capital. We put our own capital around two 50 K”
Rishikesh Kale Oct 1, 2019 ▶ 4:59
Assertion Not checkable as stated
Kale: Mailtag has over 600 paying customers
“We have more than 600 paying customers”
Rishikesh Kale Oct 1, 2019 ▶ 5:00
Prediction Not checkable as stated
Kale: Mailtag will soon reach $100K in ARR
“We will be soon reaching our revenue annual recurring revenue of a hundred K.”
Rishikesh Kale Oct 1, 2019 ▶ 5:00
Assertion Not checkable as stated
Kale: Mailtag generates around $4,500 per month in revenue
“So we are doing around, right now, we are doing around 4500 per month.”
Rishikesh Kale Oct 1, 2019 ▶ 5:32
Assertion Not checkable as stated
Paid Ads Cannot Justify Mailtag's $7 Monthly Subscription Price
“We tried running a few digital ad campaigns like a Google AdWords or Facebook in the past, but that, that's been not much efficient, and it doesn't justify the seven dollar per month cost to acquire the user because the conversion to the different sort of an a…”
Rishikesh Kale Oct 1, 2019 ▶ 6:38
Assertion Not checkable as stated
Kale: Mailtag experiences roughly 1.5% monthly logo churn
“So churn is around 1.5% right now.”
Rishikesh Kale Oct 1, 2019 ▶ 7:18
Assertion Not checkable as stated
Kale: Mailtag reduced monthly revenue churn to around 2.7%
“Revenue churn was around three percent. We have we, we've been able to reduce it to around 2.7%.”
Rishikesh Kale Oct 1, 2019 ▶ 7:30
Disclosure
Mailtag Is Currently Raising a New Funding Round
“So right now we are in between raising of funds we, we've been raising the next round of funds, and then our plan is to build more functionality to the product.”
Rishikesh Kale Oct 1, 2019 ▶ 8:24
Disclosure
Mailtag Bases Valuation on Free Installs and Users, Not Revenue
“So valuation is based on a number of installs that we have and the number of users that we have right now. So that's our source of evaluation.”
Rishikesh Kale Oct 1, 2019 ▶ 9:26
Opinion
Kale Values Mailtag Between $1M and $2M Despite $4.5K MRR
“We value it between around let's say one to two million dollars.”
Rishikesh Kale Oct 1, 2019 ▶ 14:39
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more