September 11, 2019

#71 Raising Kids Is Hard. So Is Raising a Startup.

by The Pitch

Background show artwork for The Pitch
When founder Jen Saxton landed a partnership with a big name retailer in the baby industry, she thought her startup, Tot Squad, was on the way to startup stardom. But five years into the deal, things just weren’t working out. In fact, they were a disaster. But that’s a good thing if you ask her. Jen says a stronger company has risen out of the ashes of that fiasco and she’s here to convince the investors that her new plan is worth the price of admission. 

Today’s investors are Sarah Downey, Charles Hudson, Jillian Manus, Michael Hyatt and Phil Nadel.

Where to Listen


The pivot. It’s this magical word in silicon valley. You try something, it doesn’t work. And instead of trying to make it work, you ditch it. ... Make a giant change to the business and never look back. 

Today, however. The investors are more interested in what came before the pivot ... and how that could weigh this business down.

We’ll see if entrepreneur Jen Saxton can convince them that the mistakes of her past, won't come back to haunt her.

From Gimlet, this is The Pitch. I’m Josh Muccio. Today’s investors are:

I’m Phil Nadel

Phil built companies that sold for hundreds of millions of dollars. Now he manages Forefront Venture Partners, one of the largest syndicates on AngelList.

I’m Jillian Manus

Jillian is a partner at Structure Capital, where they’ve invested $98 million in high-profile startups like Uber.

I’m Sarah Downey

Sarah’s a partner at Accomplice where they’ve invested $600 million in over 200 startups so far, one example, a company called Draftkings.

I’m Michael Hyatt

Michael built and sold two software companies for over $500 million dollars and now he invests for himself.

I’m Charles Hudson

Charles started Precursor Ventures, where he’s invested $45 million in over 100 startups to date.

Alright, on with THE PITCH.

Michael: Hi there.

Jen: Hello.

Jillian: Hi there. I'm Jillian.

Jen: Jen Sexton.

Charles: How are you, nice to meet you.

Sarah: Hey, I'm Sarah, nice to meet you.

Phil: Hey Jen, I'm Phil.

Jen: Hi Phil. Nice to meet you.

Phil: Nice to meet you.

Jen: All right. When I was five years old, I was in a car accident, sitting in the front seat of my dad's car wearing just the seatbelt when someone T-boned us right on my side of the car. Fortunately, I was uninjured, but I was one of the lucky ones.  As many as 43% of children who die in car accidents were improperly restrained. And as many as 95% of child car seats are used incorrectly. 

First-time parents, know this problem all too well. You you pick out a shiny new car seat for your shiny new baby …  But when you go to install the car seat! oh man you would not believe how infuriatingly difficult the dang things are to work with. But Jen … says her business, TotSquad has the solution.

Jen: So live now on Amazon  when you buy a car seat it asks if you would like to add the professional installation. We have hundreds of car seat installers already all over the country. uhh We did about half a million in sales last year, and we've already doubled that year to date versus last year. I've previously raised about two and a half million. And I'm seeking a million dollars now  I would love to work with a number of you guys in this room, and I'm really excited to tell you more about the business. 

Michael:  Are you saying that people don't know how to put in their car seat at all? Like this is a big problem?

Jen: Yeah. 95% are used incorrectly. 

Michael: Do you have any demo to show us? Or a picture. Show us your phone here.

Jen: Yeah, I was just gonna show you exactly how to book it on Amazon. So you just want to search, you can search any car seat 

Michael: Look car seat. Okay. I'm looking at your phone there’s a car seat  

Michael picks out his favorite car seat from the selection on Amazon. And because they’re in New York City, an additional option appears, just above the click to buy button that says “add installation.” When you click it, TotSquad will send someone to you and they will crawl into the backseat of your car, and show you how to install the carseat … the right way.

Michael:  Okay, for $89 it says here install installation for customers.

Phil: $89 to install the car seat?

Jen: So the price varies by market. We're testing different price points right now. So we've raised the price in New York City.


Phil: It seems like a lot  of money to put a car seat in no?

Jen: Yeah. So umm most of the price point we're targeting is 50 to $60 range. Like I said, in New York City, everything is more expensive. So umm...

Jillian: What percentage of the people who buy car seats actually then opt in to this?

Jen: So this service just went live a few weeks ago. And unfortunately Amazon won't share that information with us about what the conversion rate is out of the total number of purchases. But the reality is if we get 1% of middle and high income millennial moms that are purchasing items, our addressable market, or like annual sales, will be $126 million.

Phil: What percent goes to Amazon?

 Jen: Mhm. So the unit economics on a purchase, so $80 is the standard number I use  $80, Amazon gets 20% of that, so we pay them $16. We pay the car seat installer $25. So that's $41 out of the 80 are paid out. And then we keep roughly 50% just to do the customer service etc 

Phil: And what other partners are you working with other than Amazon?

Jen: So I literally two days ago signed the Walmart contract, which is so exciting.

Charles: Congratulations.

Jen: Thank you.  Umm Walmart kept telling me over and over and over again, we just want to offer this service to our customers. We don't care if we make any money it.

Michael: Wow.

Jen: But we know that customers want this. 

Jillian: Right. 

Phil: And Walmart's rolling it out to everyone?

Jen: Yep.

Phil: It'll be available everywhere?

Jen: Also we control which zip codes it shows up in  we have about 500 car seat installers over the country. But then we also just launched virtual car seat checks. So we're playing into the telehealth movement  so if you're in the hospital parking lot, baby arrived early, we will walk you through how to install your car seat over a video chat 

Michael: How do you ensure that it works?  And what's the liability on you? 

Jen: Yeah. I mean, I guess I believe that any issue is insurable. Our insurance is very hard to get. It's a huge barrier to entry to keep people from copying us. And it's very expensive.  But I think that we have a great crisis PR plan in place should an accident happen. And I have been working in this business, in this space, for going on close to eight or nine years now, and knock on wood there has never been any sort of incident, other than parents who have been in a car accident literally after driving away from having their car seat installed and the kid was uninjured. So that was the best Yelp review we ever got.

Jillian: Oh. 

Sarah: So is it just car seat installation services today? 

Phil: Yeah, that's what I was going to...

Jen: So that's all that's live right now on Amazon. So that's really our use of funds for our upcoming raise, is we want to start adding these other baby service categories.  If you think about lactation consultants, they're mostly a mom who breastfed, became passionate about it, got certified, but she's still primarily a mom. And she wants to make money doing what she's passionate about, but she doesn't know how to run a business.  So if we can aggregate all of these highly fragmented providers from all over the country and all of these different baby service categories, and become the one stop shop where parents can find all these service providers, it's just a really, really exciting opportunity. 

Phil: Is a lactation consultant the second one you'll...

Jen: So the next categories we want to launch are baby proofing, lactation and sleep consultants.

Michael: Those are huge.

Jen: Absolutely.

Michael: Lactation and sleep consultants are huge. It's amazing how many children don't latch.

Jen: It's crazy. I know, I have a nine month old.

Michael: I've been researching this.

Jillian: We told you that before! Michael's having a baby, just so you know.

Michael: Well, I'm not. 

Jillian:  And Michael's one question to me was,  do I have to feed him? Like, when do I have to feed it? And I'm thinking to myself, wow! Dude.  

Jillian: It's not a puppy, Michael.

Nows that Jillian’s properly thrown Michael under the bus, we can move on. But behind the banter, are five investors who see a problem that if solved. Could grow up to be a big business.

But the company is five years old at this point and they’ve already raised 2.5 million dollars. And to michael, for all that time and money, her baby business shouldn’t still be teething.

Michael: What did you do with two and a half million bucks?

Jen: So the original business concept, the vision I was pursuing initially, was really to be the Geek Squad of the baby industry. So when you go into Best Buy and you buy a laptop, at the cash register they ask if you would like to buy the service package. Services have to be sold in that fashion along with the product.  uhh so we actually have Geek Squad style service centers that are now open in ten cities inside Buy Buy Baby stores. So you can go in, here in Chelsea in New York City, you can get your car seat installed, you can get your stroller, your car seat cleaned, repaired. Any kind of maintenance services you need on your baby gear. 

Jillian: That's actually a really good...

Phil: You're in ten stores?

Michael: Is that part of your business today?

Jen: Yes it is. So unfortunately we've just had some challenges working with the retailer. Because  basically, in November 2014, I really realized this vision to become the Geek Squad and got buy in from the president of Buy Buy Baby that they believed in this concept of having these service centers inside the stores. And they put us through three and a half years of pilots. Like death by a thousand pilots.

Michael: Ouch.

Jen: And in that period, so last March we finally got the service center in Chelsea open.  And so right now in Chelsea when we got that service center open, it's a two story store, you're walking out of the store with your stroller or your car seat, they can't sell you the service. So you'd have to go back downstairs to the basement where the kiosk is and then swipe your credit card a second time to buy the Tot Squad service  So it is, it's like, I can't even describe how frustrating it has been to not scale my business as quickly as I thought I would because we keep they keep overpromising and underdelivering on when they're going to get the services up.

Sarah: And that's why Amazon and Walmart have been different, because they're tech first.

Jen: Exactly.

Jillian: And you obviously didn't give them an exclusivity. But I'm wondering why you waited three years and sort of, as you said, kept going...

Jen: Just kept getting strung along.

Jillian: Okay.

Phil: And you're in ten Buy Buy Babies?

Jen: Yes. Ten cities.

Phil: But they can't sell…

Jen:  So they're a product company. These retailers are designed to sell products, and they just can't, their bureaucracy, they can't get their head around how to sell services right.  Buy Buy actually tried to launch their own service center. In the middle of my pilots, they went around me and opened their own in New York City. I was just flabbergasted by the bad faith of the whole thing. umm And then I talked to a friend of mine who is in the pet space, and he said, you know what, let them do it.  Because they're going to fail and then they're going to come back to you and they're going to know how much they need you. And that is exactly what happened. 

The first incarnation of TotSquad was all about having actual people standing behind actual counters in actual stores. Even if they’re relegated to the basement. That’s why Jen is so excited to get out of the basement and onto the information superhighway …  

After the break, the investors decide if Jen’s business is ready to leave the nest. Or if it’s time to throw this baby out with the bathwater.


Welcome back.

Pivots are an important part of the way Silicon Valley works. Jen Saxton spent 2.5 million dollars going in the wrong direction. And now she wants our investors to give her money to fund this new pivot. A move away from the land brick and mortar, to the brave new world of massive online marketplaces. 

Michael: This is a pivot, which I wholly believe in, and all of here all, most of the  things we've ever done...

Jen: You gotta be resilient.

Michael: It's called the resilient pivot. So good on ya. So talk to us about your capital structure now. Like, what did you invest in, what are we investing in now?  

Jen:  So the  valuation on the two and a half million that I previously raised was about eight and a half million. And I actually am moving into a series A this fall. I'm having some really positive conversations with VCs already, but I have a bridge note open right now. So uh.

Michael: And tell us about the bridge note.

Jen: So the bridge note has  a 15 million cap. 

Michael: Okay,  Let's say we roll all the way forward to December this year, the final month. What do you think you're doing between Walmart and Amazon  in the car seats a month?

Jen: So we're taking the approach of crawl, walk, run. So we don't want to just open the floodgates and get overwhelmed and then deliver a bad service which will lead to bad reviews, etc. We really take it seriously that we have high quality vetted service pros on our platform. Which means we video interview every single one of them. They go through a background check before they get live on Amazon, etc. So I think we'll do about a million this year. We did about half a million last year 

Phil: How many orders are you getting per week? 

Jen: So again, we are only live in a couple of markets where we've turned it on, because we control which zip codes it shows. But we're doing a couple thousand dollars a week right now 

Sarah:  What about companies like Or other service providers that do pieces of daycare, lactation consultants, whatever. What's your take on them?

Jen:  There's a lot of folks that are targeting a single service category, like resale of baby gear. Or childcare. Or kids' activities  But there's nobody who's taking all of these disaggregated fragmented service pros and then aggregating them to where you can find multiple categories in one place. So that's really what we're focused on, is being the one stop shop. So I haven't really talked about the real strategy here.  we know so much about our customers. So we've serviced over 50,000 customers already. When we install a car seat, we not only know your general demographics and contact information, we know your due date, or your kid's age, height, weight, name, your vehicle make and model, your brand of your car seat and your stroller. And using all that data,   we know when the child's born, you need the lactation consultant immediately. We know about four months later, you'll need the sleep consultant. We know that six months later, you need the baby proofer. So there's all the different service pros that you need throughout the journey. And right now we're targeting the zero to five age range, but I think there's no reason in the future we can't grow with our families. Kids, once they're in preschool, need occupational and speech therapy sometimes. There's all sorts of things. They need tutors, they need language learning. There's all these services.  So that's kind of one of the goals with the big series A I’m planning to raise.

Michael: That's a smart idea. 

Jen: Thank you.

Michael: That's a good trend for you.

Jen: I'm excited. 

Aaah data! as elusive and magical as sleeping through the night! Jen wants to dream about her huge vision for TotSquad. But the investors seem more interested to know if Tot Squad can crawl, before they’ll pay to see if the business can run.

Michael: So  look, I'm, this is where I'm struggling. I like everything I'm hearing. I like you, I like this market. I believe that this thing is going to keep going.  So you, okay, granted that you will get into big data and all that kind of stuff, but that value is honestly one to two years away from real, real value. So I can't pay for that now.  so I'm struggling at the valuation, because I want to come in, but I think I'm weighed down by your previous round. You're actually, your 2.5 million which you've done, to take the pivot.

Jen: But that 2.5 million that I raised was absolutely essential to get to where we are today. Because it took years to build the relationships with the retailers to get them to create a new category.

Michael: Which didn't...

Jen: But that's where the value is.

Michael: But not really because that didn't work.  And if I was starting today, you would be starting at a, I don't know, a five, six, seven or eight million valuation. You're raising that money. And we just skip that retailer, erase that, and you just go straight to here 

Jen: Well, like I said, I am getting a lot of interest from VCs for a Series A in which I expect to raise, I have a plan for a 3 - 5 million raise, and I have a plan for an 8 - 10 million raise, in which I'd actually like to acquire a mommy blog where I can get a built in audience. 

Michael: How much of the million have you raised?

Jen: 200,000 from two emails to my existing investors.

Michael: Right. So are you open to changing your structure on that deal?

Jen: I don't think so 

Sarah: So I've just been sitting here with a lot of interest, because  I have a lot of knowledge in this space. So to say, oh, you know, we'll the data and we'll throw some machine learning on there and figure it out, it's a lot tougher than that. So I've seen it firsthand. I've seen how hard it is.  umm So I think, I.. for me, it's a pass, because the moats you describe are insurance and these partnerships that you worked on. And I don't want to undervalue those at all, it's just that my bias is like, I would like more of a technological moat  So it's a pass 

Charles: I'm also going to pass for a slightly different reason  I just think for this to work I have to be able to believe that that first product sale is a gateway into a larger relationship with the mom. And just my experience has been that  parents are picky. But what's it going to take to build a brand that's so trusted that you get, like the thumbtack of Modern Parenting?  And I guess I'm just skeptical that that brand can be built cost effectively today. That it's going to be a while before there's a brand that's so trusted that you go, I'm just going to go to them for everything  I just think I have reservations about what it would cost to build that brand 

Jen: All right  

Michael: Okay, so I'll go. So I'm going to pass, but here's why.  There's not a what I call a margin of safety in this deal. I believe I'm paying for the pivot that you made  I don't want to pay for that. I think you should do a continuation $1 million from the round that you were. So I think you're probably somewhere 6 to 8 million or whatever it is. I don't want to pay up a lot more than that right now. So for that reason I'm going to pass. But I think you're really fantastic.

Jen: Thank you.

Jillian: I'm going to ditto on what Michael said  I think right now it would be a good idea for you just to raise a million dollars  on the same valuation.

Jen: Right.

Jillian:  So I'm out. I'm out.

Jen: All right.

Charles: Phillip?

Phil: So I'm excited by your recent pivot, by your relationships with Amazon and now Walmart.  The flipside is I get concerned about Amazon putting you out of business and doing this themselves.  Amazon is not shy about doing that. They knock off top selling products all the time and do private label themselves.  They could just say, okay, now this is our service.

Jen: But Amazon only controls about 20% of the market right now. I think the fact that we're diversifying with relationships with the other retailers, . So we have some diversification away from Amazon. But I think in comparison to other markets Amazon is looking at, this one is relatively small. It's really large for us, but it's really small compared to the other things that Amazon is looking at, so it doesn't keep me up at night. 

Phil: That's good. That's a good point. I think, though, that given that  you're looking at a $15 million cap on the note, I can't get on board with that at this stage. So I’m going to pass. 

Jen: All right, I guess my question to you guys would be would this conversation have gone any differently if I'd come in here and said I'm raising a $3 - 5 million series A, are you interested in participating?

Jillian: No, you're too early for that 

Michael: Jillian's right. It's rare, but she’s right.

Jillian: And on that we'll wrap it up!

Jen: Thank you guys.

Phil: Thanks so much

[thanks and byes]  

Jen is shooed out the room so the grownups can talk.  

Even though all she heard was “no, no, no” from the investors. They wanted to say “yes, yes, yes” and give her the world...

[00:43:51] Jillian:  Now here is the most,  she was so good. And I wanted so much to invest in this.

[00:44:01] Michael: It's a mispriced deal.

[00:44:02] Jillian: Completely mispriced deal. If she had come in, I think we probably would have, well I would have been in. I would have been in. But I think she did not understand... And I'm trying to understand who advised her? Once again, where'd she come up with the 15 million?

[00:44:14] Michael: Because she can. Because she got people to buy into it.

[00:44:19] Jillian: Who bought into it? She's only done...

[00:44:20] Michael: Well, her previous investors, she said.

[00:44:21] Jillian: What? By 200,000.

[00:44:22] Michael: Listen, founders will kind of greedy up to whatever they can. And good on them.

[00:44:27] Jillian: But she didn't seem like that. 

[00:44:28] Michael: I get it.

[00:44:28] Jillian: She seemed too intelligent for that.

[00:44:30] Michael: No, all founders want a higher valuation.

[00:44:31] Charles: I think what happened is someone probably said your Series A is going to be 20. So relative to your series A, 15 is a pretty good deal if you're going to the deal at 15.

[00:44:42] Michael: Like the person who have that advice wasn't investing. And that's what drives me nuts. 

When we return, I check in with Jen, she compares Michael to a certain shark on Shark Tank, and she shares her strategy for creating investor FOMO 


Welcome back. Jen Saxton laid out a pretty good pitch for investors. But… she couldn’t close a deal because investors didn’t want to pony up for the mistakes of her past. And Jen wasn’t really willing to lower the price to accommodate.  Two months went by and I called Jen to see how she was holding up.

Jen: I remember when I left the pitch feeling a little disappointed that I didn't get a deal, but at the same time, not devastated  And when I filmed Shark Tank a few years ago, my episode never aired, I was in the same situation. It was like, "Yeah, I've got this offer, but it's just not that good of an offer." And I know I've got other options. I'm not one of those people coming on the show who's mortgaged my house and have no other options except for the money from these people in this room.  And I didn't need to lower my valuation to close the deal. 

Josh: Yeah.   On our show, the investors  They felt like they were paying for this new pivot. And Michael asked, specifically, if you'd be open to changing the structure on the deal  What did you take that to mean when he said changing the structure of the deal?

Jen: Well, I knew that he meant, "Will you lower the valuation?" And I really liked Michael. I know that sometimes people kind of perceive him as the Mr. Wonderful of the Pitch, but I really liked him. Like I thought there was a chance that him and I would work together because I thought that we really had a good chemistry. umm

Josh: I appreciate his candor. I really do.

Jen: Yeah, absolutely.  And I didn't find him to be antagonistic. Actually it's funny, when I went on Shark Tank, Mr. Wonderful also loved me. So maybe it's just some weird thing I have going. I don't know.

Josh: That's a thing. Apparently.

Jen: I've got that vibe. I don't know. 

And so when Michael asked Jen if she would “change the structure of the deal” she knew exactly what to do. Just say no!  But it takes a lot of self-confidence to stand your ground in a moment like that. That confidence is something Jen acquired with a bit of help.

Jen: And this was actually some coaching I got through a female founders group that I'm part of, was to use really big words, because there's a lot of studies out there that show that the female founders are asked more questions that are limiting, you know, like, "Well, what about liability?" instead of, "What about the opportunity?"

Josh: Right. Right, right.

Jen: And that we just tend to undersell. And so, I was coached to use these words, and so I say it a lot when I'm talking to investors, but I'm like, "This is a massive opportunity," and, "It is inevitable that somebody is going to build a marketplace in the baby services industry.  It's inevitable.  

Josh: Are you finding that the VCs that you're talking to now have no issue with the valuation that you named of 15 million,  Do you feel like it's actually attainable?

Jen: I think it's absolutely attainable. I mean  the signals I'm getting from the market support that. I've had four VC funds now ask us to move into diligence with them. So I expect I’ll have a term sheet in the next couple of weeks 

Josh: Oh Wow.  Four at once. 

Jen: Yeah. Kind of crazy! 

Josh: A little bit of FOMO there.

Jen: Yeah, which is what everybody told me you have to do is make the investors think they're going to miss out. And so, I think that really worked for me.

Josh: It was because you told them you were on the pitch, wasn't it? You were like, "I was on the pitch." 

Jen: "If you don't get in before it airs, you're going to miss out." 

Josh: [laughs]  No but really, what was your secret?

Jen: [laughs]  I honestly think it was that coaching.  Because actually, I was at this event in June, there were like 400 people here in Los Angeles. I think it was called Demystifying Venture Capital, and they were like five VCs on the panel. And I stood up and I asked a question, and I just said, "Hi, I'm Jen Saxton. I'm the founder and CEO of Tot Squad, and I'm in the middle of this venture raise. I expect to have a few term sheets in the next couple of weeks, and I just have a question about the due diligence process."

Jen: And after I asked my question, one of the VCs grabs the mic, and she says, "I'm talking to you on Friday. Don't sign a term sheet before then." I had completely BS-ed that. Like I didn't know that I was going to have a term sheet the next couple of weeks. Like I just said, "I expect or I hope to have a term sheet the next couple of weeks," and all of a sudden, I felt the frenzy. And I was like, "This strategy works. People are not kidding when they tell you to do that." 

And that strategy? Comes naturally to Jen. 

Jen: My team, at some point somebody was asked like, how would they describe me, and Ann does marketing for us said, "Jen is relentlessly optimistic." And I just love that.  Like I am absolutely a glass half-full person, and you have to be because you're-

Josh: Relentlessly optimistic.

Jen: I'm beaten down. Every day, people will tell you about your niche idea or how stupid that is, or that's not going anywhere. People will tell you mean, stupid, horrible things about your business all the time, and you have to be relentlessly optimistic to stay alive.

Josh Yeah. You know hearing you talk, it sounds like you've been relentlessly optimistic for a while now, like really just grinding. And you're kinda to the point now where things are starting to turn in your direction. It sounds like a lot of things are going your way. But that could just be that relentless optimism pouring in over the microphone, and that's all I'm hearing. umm

Jen: Oh my god, I hope not.

Josh: Is there a flip side to that? umm 

Jen: Well, I would say just in general, entrepreneurship is a roller coaster, and it has the highest highs, and the lowest lows. And I've pulled over on the side of the road and cried in my car, wondering why people are so mean to me. You know, there are absolutely bad days.  

Jen: But to answer your question, I do think we are just at a major inflection point right now and we have a ton of momentum, because the tides have shifted in our favor. And now with the two biggest retailers, Amazon and Walmart bringing Tot Squad on to provide their baby services, it's kind of raising raising the bar. 

Josh: Yeah. It feels like you're pushing the stroller down a hill now.

Jen: I hope so. I hope so. I mean, I still, one week I think I might be bankrupt and the next I think I'm worth 40 million, so every day is different, but it feels like we're moving in the right direction 

Jen says she’s still pitching vc’s and expects to see a term sheet from one of them. Any time now…

Our show is hosted by me, Josh Muccio. We’re produced by Kareem Maddox and Heather Rogers. We are edited by Blythe Terrell and Sara Sarasohn.

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