StarZero All shows Try the podcast clipper →

Aug 7, 2023 · 15m · top-founders

Deal! How She Spun SaaS out of $5.5m Agency

Ray Hames · 9m spoken Nathan Latka · 4m 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 Conversations with Nathan Latka, entrepreneur Ray Hames breaks down how she spun out Tamara.co, a private talent management SaaS platform, from her $5.5 million agency WorkSandy. She shares actionable insights on cap table restructuring, IP transfers, software development investments, and go-to-market strategies targeting the growing in-housing trend.

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 32.6% of the talking time here. How this is scored →

Nathan as informed peer 5.2 Guest teaching 3.2 Guest disagreement 0.8 Nathan pushing back 2.4
05100:0010:000:35–2:59 · Nathan as informed peer 6/10 Episode Preview: From Agency to SaaS Spinout Nathan opens with a strong market thesis predicting a multi-billion dollar freelance management company. Ray validates the thesis while elaborating on the operational complexity of managing full freelance teams rather than single gig workers.2:59–7:05 · Nathan as informed peer 7/10 Tamara Product Walkthrough and Talent Management UI Nathan demonstrates sharp industry analysis by checking WorkSandy's LinkedIn profile live, noting that doing $5.5M revenue with only 18 full-time staff implies massive freelance margins. Ray details how Tamara evolved to replace messy spreadsheet workflows.7:06–9:58 · Nathan as informed peer 6/10 Negotiating Equity and Cap Table Distribution Nathan presses into the messy mechanics of spinning out software from an agency, asking specifically about cap table distribution and whether talent was poached. Ray transparently explains the equity swap structure and why she avoided another 50/50 partnership.9:58–13:31 · Nathan as informed peer 5/10 IP Transfer, Dev Costs, and Spin-Out Finalization Nathan pins down the exact development cost invested by the agency prior to the spin-out. Ray educates on agency economics, explaining how 50% to 3x markups justify their upcoming ROI calculator and lead generation strategy.13:31–15:42 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format. Ray provides friendly, direct answers regarding her tools, habits, and advice to her younger self.0:35–2:59 · Guest teaching 3/10 Episode Preview: From Agency to SaaS Spinout Nathan opens with a strong market thesis predicting a multi-billion dollar freelance management company. Ray validates the thesis while elaborating on the operational complexity of managing full freelance teams rather than single gig workers.2:59–7:05 · Guest teaching 3/10 Tamara Product Walkthrough and Talent Management UI Nathan demonstrates sharp industry analysis by checking WorkSandy's LinkedIn profile live, noting that doing $5.5M revenue with only 18 full-time staff implies massive freelance margins. Ray details how Tamara evolved to replace messy spreadsheet workflows.7:06–9:58 · Guest teaching 4/10 Negotiating Equity and Cap Table Distribution Nathan presses into the messy mechanics of spinning out software from an agency, asking specifically about cap table distribution and whether talent was poached. Ray transparently explains the equity swap structure and why she avoided another 50/50 partnership.9:58–13:31 · Guest teaching 5/10 IP Transfer, Dev Costs, and Spin-Out Finalization Nathan pins down the exact development cost invested by the agency prior to the spin-out. Ray educates on agency economics, explaining how 50% to 3x markups justify their upcoming ROI calculator and lead generation strategy.13:31–15:42 · Guest teaching 1/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format. Ray provides friendly, direct answers regarding her tools, habits, and advice to her younger self.0:35–2:59 · Guest disagreement 1/10 Episode Preview: From Agency to SaaS Spinout Nathan opens with a strong market thesis predicting a multi-billion dollar freelance management company. Ray validates the thesis while elaborating on the operational complexity of managing full freelance teams rather than single gig workers.2:59–7:05 · Guest disagreement 1/10 Tamara Product Walkthrough and Talent Management UI Nathan demonstrates sharp industry analysis by checking WorkSandy's LinkedIn profile live, noting that doing $5.5M revenue with only 18 full-time staff implies massive freelance margins. Ray details how Tamara evolved to replace messy spreadsheet workflows.7:06–9:58 · Guest disagreement 1/10 Negotiating Equity and Cap Table Distribution Nathan presses into the messy mechanics of spinning out software from an agency, asking specifically about cap table distribution and whether talent was poached. Ray transparently explains the equity swap structure and why she avoided another 50/50 partnership.9:58–13:31 · Guest disagreement 1/10 IP Transfer, Dev Costs, and Spin-Out Finalization Nathan pins down the exact development cost invested by the agency prior to the spin-out. Ray educates on agency economics, explaining how 50% to 3x markups justify their upcoming ROI calculator and lead generation strategy.13:31–15:42 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format. Ray provides friendly, direct answers regarding her tools, habits, and advice to her younger self.0:35–2:59 · Nathan pushing back 1/10 Episode Preview: From Agency to SaaS Spinout Nathan opens with a strong market thesis predicting a multi-billion dollar freelance management company. Ray validates the thesis while elaborating on the operational complexity of managing full freelance teams rather than single gig workers.2:59–7:05 · Nathan pushing back 3/10 Tamara Product Walkthrough and Talent Management UI Nathan demonstrates sharp industry analysis by checking WorkSandy's LinkedIn profile live, noting that doing $5.5M revenue with only 18 full-time staff implies massive freelance margins. Ray details how Tamara evolved to replace messy spreadsheet workflows.7:06–9:58 · Nathan pushing back 4/10 Negotiating Equity and Cap Table Distribution Nathan presses into the messy mechanics of spinning out software from an agency, asking specifically about cap table distribution and whether talent was poached. Ray transparently explains the equity swap structure and why she avoided another 50/50 partnership.9:58–13:31 · Nathan pushing back 3/10 IP Transfer, Dev Costs, and Spin-Out Finalization Nathan pins down the exact development cost invested by the agency prior to the spin-out. Ray educates on agency economics, explaining how 50% to 3x markups justify their upcoming ROI calculator and lead generation strategy.13:31–15:42 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions Nathan runs through his standard Famous Five rapid-fire format. Ray provides friendly, direct answers regarding her tools, habits, and advice to her younger self.

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

0:00 · Nathan 59.2% · guest 40.8%0:00 · Nathan 59.2% · guest 40.8%3:00 · Nathan 23.2% · guest 76.8%3:00 · Nathan 23.2% · guest 76.8%6:00 · Nathan 29.6% · guest 70.4%6:00 · Nathan 29.6% · guest 70.4%9:00 · Nathan 19.1% · guest 80.9%9:00 · Nathan 19.1% · guest 80.9%12:00 · Nathan 15.3% · guest 84.7%12:00 · Nathan 15.3% · guest 84.7%15:00 · Nathan 97.2% · guest 2.8%15:00 · Nathan 97.2% · guest 2.8%
Sharpest disagreement ▶ 10:36 Ray clarifies dev spend was not sunk cost

Ray pushes back on the framing of development spend as a pure expense, clarifying that the agency generated subscription revenue from the tool while building it.

 Hardest push from Nathan ▶ 8:21 Nathan presses on majority ownership and team poaching

Nathan directly challenges the equity breakdown, asking if she owns over 60% and whether negotiating away top talent caused partner friction.

 Biggest teaching moment ▶ 12:45 Ray breaks down 3x agency markups

Ray educates Nathan and the audience on typical agency margins and hourly markups to explain how Tamara's ROI calculator demonstrates clear cost savings to mid-market brands.

 Nathan holds their own ▶ 6:27 Nathan deduces freelancer leverage from LinkedIn data

Nathan uses real-time research of WorkSandy's headcount to prove how effectively the agency leveraged freelancer operations to drive $5.5M in top line.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Episode Preview: From Agency to SaaS Spinout 6311 Nathan opens with a strong market thesis predicting a multi-billion dollar freelance management company. Ray validates the thesis while elaborating on the operational complexity of managing full freelance teams rather than single gig workers.
Tamara Product Walkthrough and Talent Management UI 7313 Nathan demonstrates sharp industry analysis by checking WorkSandy's LinkedIn profile live, noting that doing $5.5M revenue with only 18 full-time staff implies massive freelance margins. Ray details how Tamara evolved to replace messy spreadsheet workflows.
Negotiating Equity and Cap Table Distribution 6414 Nathan presses into the messy mechanics of spinning out software from an agency, asking specifically about cap table distribution and whether talent was poached. Ray transparently explains the equity swap structure and why she avoided another 50/50 partnership.
IP Transfer, Dev Costs, and Spin-Out Finalization 5513 Nathan pins down the exact development cost invested by the agency prior to the spin-out. Ray educates on agency economics, explaining how 50% to 3x markups justify their upcoming ROI calculator and lead generation strategy.
The Famous Five Rapid-Fire Questions 2101 Nathan runs through his standard Famous Five rapid-fire format. Ray provides friendly, direct answers regarding her tools, habits, and advice to her younger self.

Statements from this episode (7)

Prediction Not checkable as stated
Latka: Freelance management software will spawn a $1B company within five years
“I am convinced that we are within five years of somebody taking a company public with a billion in revenue or at a billion valuation because they manage freelancers and part-time talent so well.”
Nathan Latka Aug 7, 2023 ▶ 1:36
Insight
Hames: Every Talent Marketplace Struggles with Keeping Profiles Active
“Obviously keeping those profiles active is something that every talent marketplace struggles with”
Ray Hames Aug 7, 2023 ▶ 4:11
Assertion Not checkable as stated
Hames: WorkSandy generated $5 million in revenue last year
“We did five million last year in revenue.”
Ray Hames Aug 7, 2023 ▶ 5:56
Disclosure
Hames: WorkSandy received Tamara equity in exchange for IP spinout
“We made the decision that I was going to take the tech side and spin that out, and he the trade-off is that for the IP, Sandy and my co-founder have a little bit of equity on the cap table with Team Era. And, you know, and in exchange, I left the cap table of …”
Ray Hames Aug 7, 2023 ▶ 7:35
Insight
Hames: 50-50 equity splits cause confusion over who holds ultimate responsibility
“I was a fifty-fifty owner in Sandy, and sometimes that created confusion, honestly, about like, who's doing what, and who's the most vested, who has the most vested interest here, and I think that for me going into Teamera, I needed to know at the end of the d…”
Ray Hames Aug 7, 2023 ▶ 9:23
Assertion Not checkable as stated
Hames: WorkSandy Spent Just Shy of $1M Developing Tamara's Software
“I mean, like just shy of a million, just shy of a million.”
Ray Hames Aug 7, 2023 ▶ 10:24
Assertion Not checkable as stated
Hames: Surviving ad agencies charge 50% markups; 3x margins are dead
“A healthy ad agency is running the three X markup, which like hardly anybody's getting away with these days. But any agency that's still in business is running at least a 50% markup on ours.”
Ray Hames Aug 7, 2023 ▶ 12:50
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