Scaling Childcare with Tech: Winnie.com’s Blueprint for Growing with Purpose & Profit | E2005

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 9 September 2024

⏱️ 64 minutes

🔗️ Recording | iTunes | RSS

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Summary

This Week in Startups is brought to you by…

Brave Search API. Get started for free at ⁠https://www.brave.com/jason

CLA. Get started now at ⁠https://www.claconnect.com

Sprig**.** Visit https://sprig.com/twist to book a demo and get a $75 gift card.

Timestamps:

(0:00) Sara Mauskopf, CEO of Winnie joins Alex

(1:45) Winnie's evolution, pivot, and focus on childcare services (7:25) Building Winnie's database and reflections on company growth

(9:55) Brave Search API. Get started for free at ⁠https://www.brave.com/jason

(12:08) The value of transparency and growth metrics

(19:20) CLA. Get started now at ⁠https://www.claconnect.com/

(21:16) Market positioning, motivations, and goals in the childcare industry (23:30) Addressing gender dynamics and startup funding (27:34) Balancing investor expectations with business models

(29:43) Sprig. Visit https://sprig.com/twist ****to book a demo and get a $75 gift card.

(31:10) Profitability, operational efficiency, and managing costs (37:01) Marketing strategies, brand growth, and the impact of Google’s model (40:30) Adapting to changing childcare demands due to remote work (44:08) Efforts to reduce childcare costs and home-based business challenges (50:06) Balancing profitability with growth and venture capital experiences (54:00) SaaS pricing challenges and the impact of AI (58:22) Tech M&A, FTC regulations, and innovation policies

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Check out: Winnie: https://winnie.com/

Check out 2024 Inc. 5000 list: https://www.inc.com/inc5000/2024

Check out the BLS statistics: https://www.bls.gov/cps/telework.htm#data

Follow Sara:

X: https://x.com/sm

LinkedIn: https://www.linkedin.com/in/smausk/

Follow Alex:

X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Thank you to our partners:

(9:55) Brave Search API. Get started for free at ⁠https://www.brave.com/jason

(19:20) CLA. Get started now at ⁠https://www.claconnect.com/

(29:43) Sprig. Visit https://sprig.com/twist to book a demo and get a $75 gift card.

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Transcript

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0:00.0	I think there's room for lots of payers in this market. I would like to see more support from the government.
0:06.2	I would like to see more support from employers. I would pick any other market if I just wanted to like get rich. This is not the one to just get rich in necessarily.
0:16.0	It's not a really sexy market, but I'm in this because I want to improve the child care industry.
0:22.0	I want to make things better for the next generation of parents the next generation of children
0:28.0	This weekend startups is brought to you by brave if you're building AI and search-based applications,
0:35.2	train your models with the Brave Search API. Get started for free at brave.com
0:40.7	slash Jason. CA. Innovation takes balance.
0:45.0	CLAs, consultants, and wealth advisors can get you from startup to where you want to end up.
0:51.0	Get started now at CLA Connect.com slash tech.
0:55.5	And Sprigg, the product experience platform
0:59.2	that generates AI-powered opportunities
1:01.5	to continuously improve your product at scale.
1:04.4	Visit Sprig.com slash Twist to book a demo and get a $75 gift card.
1:10.3	Welcome back to this week in startups. My name is Alex. I am Alex over on X. We are joined today on the show by another person with a very good, very short Twitter handle. Her name is Sarah Moskoff. She's the co-founder and CEO over at Winnie.
1:25.4	And Sarah, if memory serves, your Twitter Handle is just S&M. Yeah?
1:30.1	Well, when you say it like that, it sounds inappropriate, but yes, SM.
1:35.0	Yes, just no and needed, just SM.
1:38.0	If you want to follow her over on Twitter, she's fantastic.
1:40.6	I've known Sarah for a long time. I've known her company Winnie for a long time and actually I got to interview you Sarah back on Equity with Tech Runge, but you're back because your company is once again on the Inc 5000 ranking very high which means that it's growing very quickly and I want to get into that.
1:58.7	But people might not know what Winnie does so if you could just rewind the clock back to 2016 when you founded the company.
2:06.4	Initial idea, learnings, pivot, and then today in a nutshell, what's Winnie?
2:11.0	Yeah, so I wish I could like go back in time and delete like the old
	...

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