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Cindy Eckert — How to Sell Your Company For One Billion Dollars (#314)
“Fuck the unicorn. Be the workhorse.” – Cindy Eckert (formerly Whitehead)
Cindy Eckert (@cindypinkceo) is an entrepreneur with $1.5 billion in exits who currently serves as the founder and CEO of The Pink Ceiling, an investment firm and consulting enterprise nicknamed the Pinkubator with a mission to invest in, launch, and build other women-led or focused businesses. She believes that access to good advice alone is not enough to change the ratio of men to women in business, and that is why she personally invested more than $15 million in 2020 alone to support the development of nine portfolio companies.
I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way. I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much regardless of gender. The negotiating techniques, the approaches to deal-making, everything that we talk about applies to entrepreneurs, period, full stop.
Earlier in her career, Cindy was the founder of Sprout Pharmaceuticals, home of Addyi, the first and only FDA-approved treatment for low sexual desire disorder in women, which was sold for one billion dollars and then reacquired in a crazy story with incredible terms that we will discuss in this conversation.
Please enjoy this wide-ranging conversation with Cindy Eckert!
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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.
Scroll below for links and show notes…
Selected Links from the Episode
Connect with Cindy Eckert:
- Cindy tells us her 2020 J.P. Morgan Healthcare Conference “do or die” story. [07:43]
- What is Cindy’s favorite business, and why? [09:41]
- How does a company instill exceptional pride in its workforce? [10:51]
- Cindy’s soup-to-nuts, three-minute commercial. [12:45]
- What does Cindy listen for when asking questions during an interview? [15:13]
- As an undergrad, how did Cindy’s business professor drive her to excel? [16:45]
- How does someone start a pharmaceutical company without a scientific background? [18:06]
- In what ways did Cindy strive to make Slate, her first pharmaceutical company, differ from other pharmaceutical companies? [19:01]
- Cindy is a card-carrying member of the Sexual Medicine Society. [20:47]
- The fortuitous story behind Slate’s development of the first long-acting testosterone (and why it was half the price of anything similar on the market at the time). [21:39]
- How Cindy tests an interviewee’s aptitude for cultural fit. [24:46]
- The six specifics Cindy seeks from a potential hire. [25:53]
- How does Cindy avoid false positives during the interview process? [26:55]
- A quirky (and possibly bold) story from Cindy’s personal experience. [28:38]
- Duck Balls? [29:55]
- Cindy gives everyone nicknames. Why? [30:42]
- Are the people so bequeathed with nicknames ever allowed to veto them? What are some of these nicknames, and how have they come about? [32:38]
- While nicknames and other constructs of irreverance can be a bonding experience among peers, what advice would Cindy give to those afraid to offend in these sensitive times? [34:38]
- What is Cindy’s nickname? [37:41]
- Cindy’s best approach for maintaining sales morale that ran counter to typical pharmaceutical techniques. [38:36]
- How is first contact made with a sales prospect, and how is a unique relationship cultivated? [39:31]
- Cindy’s team learned and borrowed from Zappos’ business model. What other businesses were especially influential? [41:58]
- If Cindy were teaching entrepreneurship to college freshmen, what book would she assign as required reading; what project would be mandatory? [42:42]
- We discuss Noah Kagan’s recommended exercise for getting comfortable with discomfort. [43:49]
- A story about Cindy’s boldest choice: fighting the FDA with her second company, Sprout. [45:40]
- Cindy explains Hypoactive Sexual Desire Disorder and what Addyi does to treat it. [47:04]
- How similar was Addyi’s genesis story to Viagra’s? [49:53]
- Why was Addyi on the verge of being shelved, and how did Cindy’s company wind up acquiring it? [50:19]
- How do royalties work in the world of pharmaceuticals? [54:59]
- What drove Cindy to get Addyi through the hoops for FDA approval after initial rejections? [56:40]
- The road less traveled for FDA approval. [59:29]
- Were the FDA’s initial reservations regarding approval of Addyi the result of being too paternalistic about a drug marketed to women? [1:00:55]
- As someone who’s sold two of her own, what advice would Cindy give to an entrepreneur on the cusp of selling their company? [1:02:50]
- What is a best efforts clause? [1:04:04]
- When selling a company, your transaction attorneys are your most important asset. [1:05:16]
- Desperation is a poor position from which to negotiate. [1:06:21]
- How did Cindy and her team at Sprout celebrate the FDA approval of Addyi? [1:09:48]
- How did Cindy prepare against the possibility of another rejection? [1:12:45]
- Another point on selling a company you care about: “Be a little bit reluctant to give it up.” [1:14:07]
- Improving deals by letting the opposition negotiate against themselves. [1:16:10]
- How did Cindy make the most of negotiating the sale of Sprout in an auction-style environment? [1:18:27]
- How did it come to pass that Cindy’s initial investors had the opportunity to buy Sprout back — after selling it two years before for one billion dollars? [1:21:15]
- What’s next for Addyi? [1:27:02]
- Rules Cindy routinely breaks as best practices. [1:27:44]
- What is The Pinkubator? [1:29:39]
- What Cindy learned from taking capital to fund her first company from someone whose practices didn’t align with her own. [1:31:01]
- What Cindy did to relieve herself of this misalignment, and how she secured further, stable investment without making it her full-time job. [1:33:07]
- How did Cindy vet investors? [1:35:52]
- What is The Pink Ceiling? [1:37:22]
- Examples of companies and products that benefit from The Pink Ceiling’s help. [1:37:44]
- What should people know about Raleigh, NC? [1:40:06]
- “Women need a voice. We need power, and money is power. Money is power to start to change things.” [1:40:50]
- Being aware of rules we’re following that we’d be better off breaking. [1:43:30]
- What class would Cindy choose to teach? [1:45:49]
- On startup founders putting in the time to earn self-confidence. [1:47:53]
- What does Cindy say to those who believe women who should dial back their femininity in the business world? [1:50:25]
- How Amanda Palmer co-opted ammunition from a hater for personal empowerment. [1:52:48]
- What book has Cindy re-read the most? [1:54:18]
- The last time Cindy cried tears of joy. [1:55:10]
- An unusual habit or absurd thing Cindy loves. [1:56:55]
- Cindy talks about growing up surrounded by superstition in Fiji. [1:57:54]
- What Cindy would cover if she had to give a TED Talk about something nobody would expect. [1:58:37]
- What does Cindy do to get back on track when she’s feeling overwhelmed or unfocused? [2:00:23]
- What would Cindy’s billboard say? [2:02:09]
- How has one of Cindy’s failures contributed to later success? [2:02:49]
- Getting in contact and parting thoughts. [2:04:07]
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46 Replies to “Cindy Eckert — How to Sell Your Company For One Billion Dollars (#314)”
From the email you sent out about your interview with Cindy: “I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender.”
I’m shocked that you’d need to include a disclaimer because – gasp! – you’re interviewing a successful CEO who also happens to be a woman. If your male listeners can’t deal with or are turned off by a successful female CEO, then let them leave your podcast, Tim. Remember the 80/20 rule?
I’m a longtime fan but am disappointed in and surprised by your language. Unless you also start using this phrasing for all of your male CEOs, then doing so for your female guests is really unfortunate. I also feel that its unfair to your podcast guests.
I’ll follow up to my own post to say that I’m glad that most of the comments, thus far, have also echoed this sentiment. I hope you read these boards, Timothy: it seems some consensus has been found.
This part of the email is absolutely required. And here is why: when I hear a mission statement of “helping only women succeed” as Pink Ceiling does, it reeks of “identity politics” and gender-based activism, which we are overfed with recently. And listening to another political opportunist isn’t what people are stocked about. So what Tim essentially said, that even if her current project SOUNDS like another identity politics play, she is an actually interesting enterpreneur, not just “We, Female Enterprenuers, rah-rah-rah” kinda of person, that usually have nothing to say but their political agenda.
To make you feel easier, someone with “Men Enterpreneurs” incubator would make me feel this way.
I only listened to this and gave it a chance because of this disclaimer and I am not alone.
David, hidden deep within the language you used to mansplain yourself is the reason why us women have to stand up to this completely obtuse rationality.
Andrew, thanks for the note back: much appreciate the personal touch. However, the email that Tim sent didn’t mention “helping only women succeed”, but rather “other women-led or focused businesses”. Not that it would have mattered one bit if he did mention that, mind you: people who tune in to Tim trust his opinion no matter WHO his guest is. If he wants a woman on his podcast who only works with women, then we’re all sure there’s a reason for that and trust him. Period.
To have to explain/apologize for this is, I maintain, doing your guests and listeners a disservice.
So we’re working with the same text, here’s the email you folks sent:
“Cindy Whitehead (@cindypinkceo) is an entrepreneur with 1.5 billion dollars in exits who currently serves as the founder and CEO of The Pink Ceiling, an investment firm and consulting enterprise nicknamed the Pinkubator with a mission to invest in, launch, and build other women-led or focused businesses. She believes that access to good advice alone is not enough to change the ratio of men to women in business, and that is why she personally invested more than 15 million dollars in 2020 alone to support the development of nine portfolio companies.
I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender. The negotiating techniques, the approaches to deal-making, everything that we talk about applies to entrepreneurs, period, full stop.
I guess I read this more as – you needed ‘a’ disclaimer to get you past this person’s buisness field without which you may not have bothered? I can relate to that – still not absorbing all the pinkness rught now . For me is wasn’t that there is a disclaimer – it’s that the disclaimer targetting only men (it didnt have to do that – as I said pink disclaimer would have been fine) reads – to many women as “‘she’s good despite / in spite of – her gender”. I dont *think Tim only wants men who believe women are a subspecies to listen to his show… am I being really naive?
I fully understand why Tim included the disclaimer, if you’re like me, then you probably skip the female interviewees, not because of some sexist reason, but because they ramble on for about 90% of the interview about getting into business as a woman. Not very relatable, so that disclaimer helped put into perspective that the interview will be centered on exit strategies, and not male dominance in the workplace. Cheers.
Are you saying that – of all the women Tim interviews most of them rambled on 90% of the time about getting into business as a woman?
I was just coming to write the same thing. The disclaimer is extremely offensive to women. Tim, please take it out! You are making the assumption that men don’t want to hear from women and that women don’t usually have much to contribute to the conversation. I’m a long time listener too and have struggled with your podcast because of subtle things like this. Either that, or make the disclaimer before every male interview that women might also (shockingly) maybe find something to gain from something a man says. Shame on you for this! Please remove it.
Pumped to listen to this. Thanks Tim. And to your point to the men: “don’t be turned off by this bio”…the evidence indicates that gender diversity on boards and in the workplace improves outcome metrics – revenue, decision-making, on and on…
The point is, women have a critical perspective to bring that will make us all more successful. That’s the reason men should pay attention.
So refreshing to see cool, incredibly smart, far from the stereotype and powerful women talking science and business in a “not so formal” environment, you have provided a platform for this woman and some other women to shine. Loved the conversation Tim.
Big fan of yours, Tim, but this kind of disclaimer should not exist in 2020, even if the majority of your fans are men.
“I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender. “
Sarah, it should not exist if it’s just a female entrepreneur, but not someone who positions themselves as gender activist and invests in women-led businesses on purpose.
MG- argh. Re: Cindy Whitehead
“I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way… ”
Well, I am a woman reading this and take offense to this particular comment. Just WHY?! It’s precisely comments like these that show complete insensitivity to a woman’s accomplishment, “irrespective of gender!” Like, why would you need to mention her being a “good CEO” as if that’s an anomaly (and if so, is that pertaining to the approx. 5% of women CEOs or the other 95ish percent?) ?
I had already garnered that from:
“she personally invested more than 15 million dollars in 2020 alone to support the development of nine portfolio companies.” Just not sure why it needed to be prefaced as if by some test pass of sorts. Just a thougt! Thanks very much!
I really enjoy the podcast but totally take exception to the part where you tell men to not be turned off by the bio. I get what you are saying but it really strikes a chord that you make an effort to appeal to your male audience. Are you going to include that disclaimer in EVERY OTHER podcast for female listeners that feature men? Don’t forget your female listeners are out there and it feels like a backhanded compliment to feature a high performing woman and include a disclaimer that she’s “not so bad”, which is how that paragraph reads.
He only needs to include this disclaimer for people with clearly gender-based missions like Pink Ceiling does:
“CEO of The Pink Ceiling, an investment firm and consulting enterprise nicknamed the Pinkubator with a mission to invest in, launch, and build other women-led or focused businesses.”
How would you feel about a company investing only in men-run businesses. Basically this disclaimer was that she really is an interesting entrepreneur not yet another “diversity” gender-activist that has nothing to say, other that political agenda.
I am also turned off by the sound of pink this and that – and also might have chosen not to hear this one. A disclaimer might have helped me to take the time.
However I – like a lot of women- found *this disclaimer really uncomfortable.
I think some of it is probably ontological – so Tim maybe didn’t mean – “You should listen to this woman because *I picked her – despite her being a woman”. But that *is how it comes across to many of the people here. He could have said:
“I should mention right off the bat that if you are turned off by the… pinkness of it all- I wanted to have Cindy on the show because her way of doing business, and the success she has achieved is remarkable and we can all learn from her. The negotiating techniques, the approaches to deal-making, everything that we talk about applies to entrepreneurs, period, full stop”.
“I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender. The negotiating techniques, the approaches to deal-making, everything that we talk about applies to entrepreneurs, period, full stop”.
I think maybe you don’t hear in the disclaimer what some of the women here hear – and maybe we just have to accept that that is because you aren’t a woman – we do experience life in different ways.
Andrew, you keep saying Tim “needs to include this disclaimer” or that it’s “absolutely required” but neither of those things is true and, worse, you aren’t hearing the respectful feedback that Tim is receiving — from both men and women — about his unfortunate email.
You might want to check your insistence that Tim needs to do this or do that and instead ask yourself why at least ten different people on this board (the majority of posts, in fact) all say the same thing: his language wasn’t cool.
Please stop being stubborn and start listening: we don’t CARE if Cynthia prefers to pursue women-led companies or ONLY work with women-led companies. What we care about is that Tim found someone awesome he wants us to hear and meet.
This was a great interview and I enjoyed it. I am writing to applaud that you included this advice:
“I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way ”
— If you had not written that, I would not have listened and I would have missed a great interview.
Also, I live near Raleigh and it is a great – and growing – place for entrepreneurs. You should come check it out.
„I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender. The negotiating techniques, the approaches to deal-making, everything that we talk about applies to entrepreneurs, period, full stop.“
… she is a good ceo and entrepreneur, very much irrespective of gender? Don‘t let this bio turn you off?
Well, I wonder — why should it turn male listeners off? Because they can‘t take it that there is a very successful person out there choosing purposefully female business only? And with a very good reason at that, too? Or because these listeners might think „Oh okay, I won‘t learn much from her then?“
Have you ever written something similar to your female audience?
It‘s offensive. But I guess it‘s honest and real, too – you felt the need to write this because you estimated a big enough number of male listeners who wouldn‘t listen otherwise. Someone already thanked you for that.
Hi Jon – I’m curious to know why you would not have listened to this episode without Tim’s disclaimer? I’m genuinely trying to understand a different point of view.
First, I am replying with the assumption that you are sincere – that doesn’t always happen on the internet.
I from Tim that not all of his work is a good ‘fit’ for all of his audience. As I recall, he has said that his goal is for 10% of his audience to be interested in any given topic. I think that comment was before he started doing pod-casts though. So whenever Tim posts something, I have to look at the topic / person and decide if I am going to invest my time into it. Most of the time, I don’t.
I am interested in knowledge related to business and business people, so Cindy’s interview passed the first check. If the intro paragraph had not mentioned Cindy’s limiting focus on women-led activities, I don’t think the ‘disclaimer’ would have been necessary. (A bit of a double-negative there, I guess.)
When I read the intro, my mind went “well, I’m not a woman and not married, so this isn’t something that immediately benefits me.”. The disclaimer clarified that focus and motivated me to give the interview a try.
Cindy’s strong character, personality, and charisma were obvious to me within the first minute – I knew I would listen to the entire interview, regardless of whether it focused exclusively on women. By contrast, I offer the Karlie Kloss interview. (I am a software engineer, so the topic fit my interests.) I wonder if Karlie’s intro – which didn’t include a disclaimer – might have benefited from one. But then again, I listened to some of that interview, but got less than halfway through. It wasn’t engaging enough. Tim’s a smart man, perhaps he recognized that Cindy’s interview was worthwhile, regardless of gender focus?
thanks for asking, hopefully, this helps your understanding a bit.
A rather late thank you, Jon. But I am/was sincere and appreciate your thoughtful response. In these divided times, I am attempting to deepen my skill set on understanding others who may have a rather different perspective/opinion from my own.
Hey Tim! Quite disappointed in the appeal to guys to please listen even if this is a female billionaire. Your comments sounded as if, because she is female, she wouldn’t have the same qualities as a male, and therefore you must reassure your audience. As a female fan who listens to plenty of men on your show without your reassurance that it’s worth it, I feel taken for granted and am surprised that this sort of caveat would be necessary in the 21st century community you are building and leading.
Awesome interview thank you. Great questions and fascinating answers
[Moderator: additional text removed.]
Iam from Sri Lanka, following you for an hour for your podcast , I read your book 4 hour work week even before I get to know you through podcasts.
I am an architecture student in university of Moratuwa 4th year so get through this your works been very help full to me .
I’d be really interested in how you would apply your principles to making it far in the music industry- from mastering your skills, to creating awesome music and finally getting out there and going far in the music world. Thank you so much for everything you’ve done, you’re a true inspiration!
“I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender. ….”
Wow…. really, really, really, really, really, really, really, really, really, really, really BAD.
I enjoyed your book, Tribe of Mentors, and am starting to try to add podcasts to my exercise routine, so I’m starting with yours. I have only listened to a few, and I am really enjoying them. I wanted to give you feedback about your Cindy Whitehead interview, however, from a woman’s perspective. It struck me as odd that you felt the need to explain to your male viewers that, even though Cindy has some female-centric focus, she might have something interesting to say to men. Really? Cindy’s resume speaks volumes about her business acumen and amazing success. Your implication that a self-made billionaire is somehow less-than because her current business model has some female focus smacks of patriarchy. The thing that really prompted me to write, though, is how much you interrupt her. It reminded me of the widely-circulated video of the moderator constantly interrupting a female panelist as he explained her own research to her until an audience member yelled out, “Let her speak!” I am only about 20 minutes into the podcast, and despite your discussion of silence as a powerful tool and Cindy’s discussion of how much you can learn from people by listening, you talk over her constantly. Granted, I have not listened to a ton of your podcasts, but I wonder if you do the same with men. I said aloud more than once, “Tim — please let her talk! I want to hear what she has to say.” I do very much appreciate the perspective you bring, though, and am loving your 5-bullet Friday emails. You’re doing good work. Just wanted to let you know my perspective.
I appreciate all the work you have done; my hats off to you. However, I see a teachable moment that needs to happen here. Your disclaimer: “I should mention right off the bat that if you’re a guy, don’t let this bio turn you off in any way. I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much regardless of gender” is troublesome. I understand you’re aiming to teach men who otherwise would pass up learning about a powerful woman, but the language used here suggests that your thought process aligns with these men because of the phrase: “very much regardless of gender”. To bring up gender in a way that says: hey regardless of gender, what she has done, matters, happens to be saying the opposite. It’s like the saying the most common phrase women hear most of their life: “you’re good…for a girl”. Language is a tricky climate to navigate, but should not be left unaddressed if something disagreeable is happening. I encourage you to rethink the way you express yourself concerning tricky topics; you don’t want your followers to be turned off by this moment.
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