StarZero All shows Try the podcast clipper →

Oct 29, 2021 · 17m · top-founders

How Lately Plans to Break $1m in ARR, Raising Now at $10m Valuation

Kate Bradley-Chernis · 9m spoken Nathan Latka · 5m spoken
0:00 / 0:00

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

Kate Bradley-Chernis, founder and CEO of Lately, joins Nathan Latka to break down Lately's AI content engine, revenue metrics, and strategic transition toward an unbundled self-service model supported by 18 months of cash runway and a $10 million valuation cap.

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 34.9% of the talking time here. How this is scored →

Nathan as informed peer 5.8 Guest teaching 3.8 Guest disagreement 2.5 Nathan pushing back 4.7
05100:0010:000:52–3:10 · Nathan as informed peer 4/10 The AI Engine and Applying Neuroscience to Writing Kate details how her background in rock radio and neuroscience informs the AI's content-generation algorithms. Nathan listens and prompts without disputing her premise.3:10–5:34 · Nathan as informed peer 6/10 Customer Trends, Category Creation, and Platform Decoupling Nathan presses on customer count drops and challenges Kate on why past investors thought she was crazy despite prior funding. Kate reframes the business as category-creating rather than just a social media scheduler.5:35–7:36 · Nathan as informed peer 7/10 Financial Performance and Pivoting to Self-Service Gamification Nathan interrupts to drill down into exact customer numbers, revenue drop from 94k to 79k MRR, and previous valuation multiples. Kate explains the shift to self-service gamification based on cohort churn data.7:37–10:13 · Nathan as informed peer 7/10 Operational Runway and Managing Capital in Cockroach Mode Nathan dissects gross vs net burn rate to clarify Kate's actual monthly cash dynamics and runway. Kate acknowledges living in cockroach mode while paying back deferred salaries and loans.10:17–15:07 · Nathan as informed peer 7/10 Convertible Note Oversubscription and Cap Table Distribution Nathan performs rapid cap table dilution calculations and provocatively asks why she doesn't sell to Hootsuite for 5 million dollars. Kate openly vents about fundraising hurdles, unpaid cofounders, and churn challenges.15:07–16:49 · Nathan as informed peer 4/10 Famous Five Rapid-Fire Questions with Kate Bradley-Chernis Nathan runs through the Famous Five rapid-fire questions, gently redirecting when Kate struggles with book titles and sleep metrics. Kate brings strong personality and candor to her answers.0:52–3:10 · Guest teaching 6/10 The AI Engine and Applying Neuroscience to Writing Kate details how her background in rock radio and neuroscience informs the AI's content-generation algorithms. Nathan listens and prompts without disputing her premise.3:10–5:34 · Guest teaching 5/10 Customer Trends, Category Creation, and Platform Decoupling Nathan presses on customer count drops and challenges Kate on why past investors thought she was crazy despite prior funding. Kate reframes the business as category-creating rather than just a social media scheduler.5:35–7:36 · Guest teaching 3/10 Financial Performance and Pivoting to Self-Service Gamification Nathan interrupts to drill down into exact customer numbers, revenue drop from 94k to 79k MRR, and previous valuation multiples. Kate explains the shift to self-service gamification based on cohort churn data.7:37–10:13 · Guest teaching 3/10 Operational Runway and Managing Capital in Cockroach Mode Nathan dissects gross vs net burn rate to clarify Kate's actual monthly cash dynamics and runway. Kate acknowledges living in cockroach mode while paying back deferred salaries and loans.10:17–15:07 · Guest teaching 4/10 Convertible Note Oversubscription and Cap Table Distribution Nathan performs rapid cap table dilution calculations and provocatively asks why she doesn't sell to Hootsuite for 5 million dollars. Kate openly vents about fundraising hurdles, unpaid cofounders, and churn challenges.15:07–16:49 · Guest teaching 2/10 Famous Five Rapid-Fire Questions with Kate Bradley-Chernis Nathan runs through the Famous Five rapid-fire questions, gently redirecting when Kate struggles with book titles and sleep metrics. Kate brings strong personality and candor to her answers.0:52–3:10 · Guest disagreement 1/10 The AI Engine and Applying Neuroscience to Writing Kate details how her background in rock radio and neuroscience informs the AI's content-generation algorithms. Nathan listens and prompts without disputing her premise.3:10–5:34 · Guest disagreement 3/10 Customer Trends, Category Creation, and Platform Decoupling Nathan presses on customer count drops and challenges Kate on why past investors thought she was crazy despite prior funding. Kate reframes the business as category-creating rather than just a social media scheduler.5:35–7:36 · Guest disagreement 2/10 Financial Performance and Pivoting to Self-Service Gamification Nathan interrupts to drill down into exact customer numbers, revenue drop from 94k to 79k MRR, and previous valuation multiples. Kate explains the shift to self-service gamification based on cohort churn data.7:37–10:13 · Guest disagreement 2/10 Operational Runway and Managing Capital in Cockroach Mode Nathan dissects gross vs net burn rate to clarify Kate's actual monthly cash dynamics and runway. Kate acknowledges living in cockroach mode while paying back deferred salaries and loans.10:17–15:07 · Guest disagreement 4/10 Convertible Note Oversubscription and Cap Table Distribution Nathan performs rapid cap table dilution calculations and provocatively asks why she doesn't sell to Hootsuite for 5 million dollars. Kate openly vents about fundraising hurdles, unpaid cofounders, and churn challenges.15:07–16:49 · Guest disagreement 3/10 Famous Five Rapid-Fire Questions with Kate Bradley-Chernis Nathan runs through the Famous Five rapid-fire questions, gently redirecting when Kate struggles with book titles and sleep metrics. Kate brings strong personality and candor to her answers.0:52–3:10 · Nathan pushing back 1/10 The AI Engine and Applying Neuroscience to Writing Kate details how her background in rock radio and neuroscience informs the AI's content-generation algorithms. Nathan listens and prompts without disputing her premise.3:10–5:34 · Nathan pushing back 6/10 Customer Trends, Category Creation, and Platform Decoupling Nathan presses on customer count drops and challenges Kate on why past investors thought she was crazy despite prior funding. Kate reframes the business as category-creating rather than just a social media scheduler.5:35–7:36 · Nathan pushing back 7/10 Financial Performance and Pivoting to Self-Service Gamification Nathan interrupts to drill down into exact customer numbers, revenue drop from 94k to 79k MRR, and previous valuation multiples. Kate explains the shift to self-service gamification based on cohort churn data.7:37–10:13 · Nathan pushing back 5/10 Operational Runway and Managing Capital in Cockroach Mode Nathan dissects gross vs net burn rate to clarify Kate's actual monthly cash dynamics and runway. Kate acknowledges living in cockroach mode while paying back deferred salaries and loans.10:17–15:07 · Nathan pushing back 6/10 Convertible Note Oversubscription and Cap Table Distribution Nathan performs rapid cap table dilution calculations and provocatively asks why she doesn't sell to Hootsuite for 5 million dollars. Kate openly vents about fundraising hurdles, unpaid cofounders, and churn challenges.15:07–16:49 · Nathan pushing back 3/10 Famous Five Rapid-Fire Questions with Kate Bradley-Chernis Nathan runs through the Famous Five rapid-fire questions, gently redirecting when Kate struggles with book titles and sleep metrics. Kate brings strong personality and candor to her answers.

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

0:00 · Nathan 36.3% · guest 63.7%0:00 · Nathan 36.3% · guest 63.7%3:00 · Nathan 19.8% · guest 80.2%3:00 · Nathan 19.8% · guest 80.2%6:00 · Nathan 37.9% · guest 62.1%6:00 · Nathan 37.9% · guest 62.1%9:00 · Nathan 59.2% · guest 40.8%9:00 · Nathan 59.2% · guest 40.8%12:00 · Nathan 17.4% · guest 82.6%12:00 · Nathan 17.4% · guest 82.6%15:00 · Nathan 41.8% · guest 58.2%15:00 · Nathan 41.8% · guest 58.2%
Sharpest disagreement ▶ 10:51 Kate explains fundraising reality as a female founder

Kate forcefully explains why her equity is only 38%, pointing out that female founders have to beg, borrow, and steal with messy angel cap tables.

 Hardest push from Nathan ▶ 5:34 Nathan cuts in to demand exact financial metrics

Nathan abruptly halts Kate's platform narrative to pin down precise customer counts, ARPU, and revenue drops.

 Biggest teaching moment ▶ 1:35 Kate explains the neuroscience of radio voice and trust

Kate walks Nathan through the cognitive science of sound frequencies and how triggering nostalgia builds trust to drive purchases.

 Nathan holds their own ▶ 13:21 Nathan calculates founder cap table dilution on the fly

Nathan instantly calculates co-founder equity shares by applying an estimated 50% cumulative dilution to original ownership percentages.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
The AI Engine and Applying Neuroscience to Writing 4611 Kate details how her background in rock radio and neuroscience informs the AI's content-generation algorithms. Nathan listens and prompts without disputing her premise.
Customer Trends, Category Creation, and Platform Decoupling 6536 Nathan presses on customer count drops and challenges Kate on why past investors thought she was crazy despite prior funding. Kate reframes the business as category-creating rather than just a social media scheduler.
Financial Performance and Pivoting to Self-Service Gamification 7327 Nathan interrupts to drill down into exact customer numbers, revenue drop from 94k to 79k MRR, and previous valuation multiples. Kate explains the shift to self-service gamification based on cohort churn data.
Operational Runway and Managing Capital in Cockroach Mode 7325 Nathan dissects gross vs net burn rate to clarify Kate's actual monthly cash dynamics and runway. Kate acknowledges living in cockroach mode while paying back deferred salaries and loans.
Convertible Note Oversubscription and Cap Table Distribution 7446 Nathan performs rapid cap table dilution calculations and provocatively asks why she doesn't sell to Hootsuite for 5 million dollars. Kate openly vents about fundraising hurdles, unpaid cofounders, and churn challenges.
Famous Five Rapid-Fire Questions with Kate Bradley-Chernis 4233 Nathan runs through the Famous Five rapid-fire questions, gently redirecting when Kate struggles with book titles and sleep metrics. Kate brings strong personality and candor to her answers.

Statements from this episode (12)

Disclosure
Lately's AI is Trained on Founder Kate Bradley-Chernis's Writing Rules
“So the way Lely's AI works is it first learns from me. I've written thousands of radio scripts and fiction writing major, and it learns from my best practices, which I've listed out for my whole team to Replicate. And so the AI gives us what we need, and then …”
Kate Bradley-Chernis Oct 29, 2021 ▶ 2:38
Assertion Not checkable as stated
Bradley-Chernis: Lately currently has 358 paying customers
“So we have 358 customers.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 3:18
Disclosure
Bradley-Chernis: Lately was invited to Stage 2 Capital accelerator without applying
“He led the first ever accelerator from stage two capital this summer. 700 companies were applying. We didn't apply. They just actually asked us to be a part of it, which is great.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 3:54
Disclosure
Bradley-Chernis: Managing Facebook and LinkedIn integrations absorbed 75% of Lately's resources
“And that actually, 75% of my headache as far as resources go, is just dealing with Facebook and LinkedIn and all their bullshit, right? And I didn't understand that Lately could actually function and live without that, so it could be an extension of all the ot…”
Kate Bradley-Chernis Oct 29, 2021 ▶ 5:08
Assertion Not checkable as stated
Bradley-Chernis: Lately MRR is $79k, Down from $94k Peak
“MRR is at 79,000. We were up to 94 and we dropped.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 5:47
Assertion Supported
Bradley-Chernis: Lately Has Raised $3.3M in Total Capital
“So actually, actually I've raised 3.3000000 now.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 6:04
Assertion Not checkable as stated
Bradley-Chernis: Lately has 18 months of runway on $48K burn
“Oh yeah, I have 18 months right now worth of runway, and that's in part, basically my burn is about 48,000, so every 50 K gives me three months.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 7:44
Disclosure
Bradley-Chernis: Lately is raising just under $700K on $10M cap
“I was raising two 50 and I got oversubscribed. So we're now at five 35, six, just under 700.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 10:21
Disclosure
Bradley-Chernis: Founder owns around 38% equity in Lately
“Low, actually. I need to be re-optioned, so I'm around 38%, I believe.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 10:48
Disclosure
Bradley-Chernis: Lately cap table has roughly 65 angel investors
“So I've raised multiple rounds, but all between 250,750, all angel rounds, and I have a lot of, I mean, my cap table is messy. There's probably 65 people in it.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 10:57
Disclosure
Bradley-Chernis Details Lately's Initial 60-20-15-5 Co-Founder Equity Split
“When we first started, it was I'm eight. No, sorry. Steve, 20. I do math backwards. Jason, 15. Brian, five. And then I'm the rest. So that's the ratios.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 13:23
Assertion Not checkable as stated
Bradley-Chernis: Lately maintains 98% sales conversion despite high churn
“Like I've, I still have that 98% sales conversion. I still have that shit, right? Thank God. That's the AI doing his job. But I have a leaky bucket.”
Kate Bradley-Chernis Oct 29, 2021 ▶ 14:49
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