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Jan 27, 2022 · 18m · top-founders

HR Tech Company Raises $2.5m on $18m Helping 20 Enterprises Hire Better

Raphael Danilo · 11m spoken Nathan Latka · 5m spoken
0:00 / 0:00

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In this interview with Nathan Latka, Yobs co-founder and CEO Raphael Danilo discusses how his interview intelligence platform scaled to $20,000 in monthly recurring revenue and secured a $2.5 million seed round. Danilo shares key insights into product-led growth, enterprise contract management, and navigating competition in the HR tech space.

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 31.4% of the talking time here. How this is scored →

Nathan as informed peer 5.2 Guest teaching 2.0 Guest disagreement 1.4 Nathan pushing back 3.2
05100:0010:000:45–6:55 · Nathan as informed peer 6/10 Introducing Raphael Danilo and the Evening Fund Nathan inquires about Raphael's side angel fund before digging into Yobs' business model and pricing. He probes Raphael on whether they are pre-revenue and why enterprise customers are charged while high-growth startups get freemium access.6:55–9:02 · Nathan as informed peer 5/10 Company Origins and Team Composition The conversation covers company founding details and team structure. Nathan checks whether core transcription algorithms are proprietary or third-party vendor integrations.9:04–12:14 · Nathan as informed peer 6/10 Sponsor Message: Ramp Corporate Spend Management Following a sponsor read, Raphael explains how Nissan became an early enterprise client. Nathan promptly calculates estimated MRR of $20,000 based on 20 enterprise accounts paying $1,000 per month.12:15–17:03 · Nathan as informed peer 7/10 Product-Led Growth and Market Competition Nathan deduces an $18M-$20M valuation cap on Raphael's $2.5M SAFE note and questions taking the high-expectation venture route over remaining default alive and profitable. Raphael defends the venture-backed land-grab approach.17:04–17:58 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions Nathan concludes the interview with the standard rapid-fire Famous Five questions where Raphael reveals he is 23 years old.0:45–6:55 · Guest teaching 3/10 Introducing Raphael Danilo and the Evening Fund Nathan inquires about Raphael's side angel fund before digging into Yobs' business model and pricing. He probes Raphael on whether they are pre-revenue and why enterprise customers are charged while high-growth startups get freemium access.6:55–9:02 · Guest teaching 2/10 Company Origins and Team Composition The conversation covers company founding details and team structure. Nathan checks whether core transcription algorithms are proprietary or third-party vendor integrations.9:04–12:14 · Guest teaching 2/10 Sponsor Message: Ramp Corporate Spend Management Following a sponsor read, Raphael explains how Nissan became an early enterprise client. Nathan promptly calculates estimated MRR of $20,000 based on 20 enterprise accounts paying $1,000 per month.12:15–17:03 · Guest teaching 3/10 Product-Led Growth and Market Competition Nathan deduces an $18M-$20M valuation cap on Raphael's $2.5M SAFE note and questions taking the high-expectation venture route over remaining default alive and profitable. Raphael defends the venture-backed land-grab approach.17:04–17:58 · Guest teaching 0/10 The Famous Five Rapid-Fire Questions Nathan concludes the interview with the standard rapid-fire Famous Five questions where Raphael reveals he is 23 years old.0:45–6:55 · Guest disagreement 2/10 Introducing Raphael Danilo and the Evening Fund Nathan inquires about Raphael's side angel fund before digging into Yobs' business model and pricing. He probes Raphael on whether they are pre-revenue and why enterprise customers are charged while high-growth startups get freemium access.6:55–9:02 · Guest disagreement 1/10 Company Origins and Team Composition The conversation covers company founding details and team structure. Nathan checks whether core transcription algorithms are proprietary or third-party vendor integrations.9:04–12:14 · Guest disagreement 1/10 Sponsor Message: Ramp Corporate Spend Management Following a sponsor read, Raphael explains how Nissan became an early enterprise client. Nathan promptly calculates estimated MRR of $20,000 based on 20 enterprise accounts paying $1,000 per month.12:15–17:03 · Guest disagreement 3/10 Product-Led Growth and Market Competition Nathan deduces an $18M-$20M valuation cap on Raphael's $2.5M SAFE note and questions taking the high-expectation venture route over remaining default alive and profitable. Raphael defends the venture-backed land-grab approach.17:04–17:58 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions Nathan concludes the interview with the standard rapid-fire Famous Five questions where Raphael reveals he is 23 years old.0:45–6:55 · Nathan pushing back 4/10 Introducing Raphael Danilo and the Evening Fund Nathan inquires about Raphael's side angel fund before digging into Yobs' business model and pricing. He probes Raphael on whether they are pre-revenue and why enterprise customers are charged while high-growth startups get freemium access.6:55–9:02 · Nathan pushing back 2/10 Company Origins and Team Composition The conversation covers company founding details and team structure. Nathan checks whether core transcription algorithms are proprietary or third-party vendor integrations.9:04–12:14 · Nathan pushing back 3/10 Sponsor Message: Ramp Corporate Spend Management Following a sponsor read, Raphael explains how Nissan became an early enterprise client. Nathan promptly calculates estimated MRR of $20,000 based on 20 enterprise accounts paying $1,000 per month.12:15–17:03 · Nathan pushing back 6/10 Product-Led Growth and Market Competition Nathan deduces an $18M-$20M valuation cap on Raphael's $2.5M SAFE note and questions taking the high-expectation venture route over remaining default alive and profitable. Raphael defends the venture-backed land-grab approach.17:04–17:58 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions Nathan concludes the interview with the standard rapid-fire Famous Five questions where Raphael reveals he is 23 years old.

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

0:00 · Nathan 42.4% · guest 57.6%0:00 · Nathan 42.4% · guest 57.6%3:00 · Nathan 13% · guest 87%3:00 · Nathan 13% · guest 87%6:00 · Nathan 15.7% · guest 84.3%6:00 · Nathan 15.7% · guest 84.3%9:00 · Nathan 62.8% · guest 37.2%9:00 · Nathan 62.8% · guest 37.2%12:00 · Nathan 17.3% · guest 82.7%12:00 · Nathan 17.3% · guest 82.7%15:00 · Nathan 28.6% · guest 71.4%15:00 · Nathan 28.6% · guest 71.4%18:00 · Nathan 97.7% · guest 2.3%18:00 · Nathan 97.7% · guest 2.3%
Sharpest disagreement ▶ 16:05 Raphael defends venture funding over bootstrapping

Raphael reframes Nathan's critique of venture funding, arguing that raising venture capital is specifically what affords the runway to offer freemium tiers and win the long game.

 Hardest push from Nathan ▶ 15:54 Nathan challenges venture treadmill vs cashflow positive optionality

Nathan refuses the narrative that an $18M-$20M valuation cap is purely advantageous, pushing back that high caps reduce optionality and force rapid growth or death.

 Biggest teaching moment ▶ 2:41 Raphael explains error rates and velocity in remote interviews

Raphael breaks down specific recruiting data regarding 50% post-hire conclusion error rates and how interview latency accounts for 60-80% of hiring delays.

 Nathan holds their own ▶ 8:10 Nathan calculates implied valuation cap from SAFE dilution norms

Nathan applies venture dilution benchmarks of 10-20% directly to Raphael's $2.5M seed round to immediately estimate the implied $18M-$20M valuation cap.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Raphael Danilo and the Evening Fund 6324 Nathan inquires about Raphael's side angel fund before digging into Yobs' business model and pricing. He probes Raphael on whether they are pre-revenue and why enterprise customers are charged while high-growth startups get freemium access.
Company Origins and Team Composition 5212 The conversation covers company founding details and team structure. Nathan checks whether core transcription algorithms are proprietary or third-party vendor integrations.
Sponsor Message: Ramp Corporate Spend Management 6213 Following a sponsor read, Raphael explains how Nissan became an early enterprise client. Nathan promptly calculates estimated MRR of $20,000 based on 20 enterprise accounts paying $1,000 per month.
Product-Led Growth and Market Competition 7336 Nathan deduces an $18M-$20M valuation cap on Raphael's $2.5M SAFE note and questions taking the high-expectation venture route over remaining default alive and profitable. Raphael defends the venture-backed land-grab approach.
The Famous Five Rapid-Fire Questions 2001 Nathan concludes the interview with the standard rapid-fire Famous Five questions where Raphael reveals he is 23 years old.

Statements from this episode (14)

Disclosure
Danilo: Evening Fund made about 25 investments in 2021
“Evening Fund is something that I started just earlier this year. And we've done about 25 investments so far in 2021.”
Raphael Danilo Jan 27, 2022 ▶ 1:16
Disclosure
Danilo: Bain Capital is a limited partner in Evening Fund
“Bain Capital is one that I can name. And then, yeah, there's a couple of other kind of like multi-stage funds that are LPs in the fund.”
Raphael Danilo Jan 27, 2022 ▶ 2:04
Disclosure
Danilo: Evening Fund backed its first unicorn within a year
“And we actually got our first unicorn a month ago after less than a year of investing.”
Raphael Danilo Jan 27, 2022 ▶ 2:28
Assertion Not checkable as stated
Danilo: 50% of candidate interview conclusions prove untrue post-hire
“About like 50% of interviews basically have a conclusion that doesn't end up being true post hire.”
Raphael Danilo Jan 27, 2022 ▶ 2:42
Disclosure
Danilo: Yobs enterprise accounts generate $10,000 to $60,000 annually
“So our enterprise accounts are in the five figure annual contract value. So I mean, it depends, but it's kind of like 10 K per year onwards. So roughly a thousand dollars a month up to like 5000 dollars a month.”
Raphael Danilo Jan 27, 2022 ▶ 6:19
Assertion Not checkable as stated
Danilo: Yobs has a team of 12 people
“We have 12 people on the team.”
Raphael Danilo Jan 27, 2022 ▶ 8:42
Insight
Danilo: Pursuing enterprise customers early slows down product-market fit
“We did it, you know, exactly the other way where we started with fortune to 500 accounts, which had its pros namely that you can get really big contracts really quickly. I think like as, Like, you know, just get ready to get bogged down. And also it's like a l…”
Raphael Danilo Jan 27, 2022 ▶ 11:14
Assertion Not checkable as stated
Danilo: Yobs generates approximately $20,000 in monthly recurring revenue
“Yeah, that's about right. Yeah.”
Raphael Danilo Jan 27, 2022 ▶ 12:08
Assertion Not checkable as stated
Danilo: Yobs grew its revenue roughly 3x year-over-year
“We roughly three X since last year.”
Raphael Danilo Jan 27, 2022 ▶ 12:15
Assertion Supported
Danilo: Yobs competitor Clovers raised between $10M and $30M
“You know, there's a company called Clovers out of LA that just raised a good amount of funding from like Solid investors and a couple of others. And, you know, they're, they've raised like, you know, 10 to thirty million, you know, roughly is the range.”
Raphael Danilo Jan 27, 2022 ▶ 12:49
Disclosure
Danilo: Yobs raised a $2.5M seed round from operator angels
“We just raised our seed round earlier this year. So we ended up raising two and a half million mostly from, you know, angel investor operators”
Raphael Danilo Jan 27, 2022 ▶ 14:08
Disclosure
Danilo: Adam Grant invested as an angel in Yobs
“Had a couple of, you know, cool kind of like superstar angels, like Adam Grant come in who've been awesome to work with.”
Raphael Danilo Jan 27, 2022 ▶ 14:41
Insight
Danilo: Valuation caps of $10M vs $18M rarely impact venture returns
“We're looking for these like one billion or ten billion dollar companies when we're doing venture investments, because 80% of companies are going to die at that startup stage. So whether you pay 10 or eighteen million on a cap is not really like, that's not wh…”
Raphael Danilo Jan 27, 2022 ▶ 15:36
Prediction Not checkable as stated
Danilo: A free tier strategy beats competitors charging $10,000 upfront
“Raising venture funding is what allowed us to play that long game in terms of, like, having a free plan, which I think in the long run is what's going to allow us to win, because while everybody's going to be focused on charging 10,000 dollars for a product th…”
Raphael Danilo Jan 27, 2022 ▶ 16:12
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