The entrepreneur’s guide to a good divorce settlement

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Here’s what happens in every meeting I have with investors: They ask about my divorce.

Many people ask about my divorce. Usually it’s because the person cares about me. But with the investors, there is no pretense. They just want to know if Nino is going to get a large percentage of my stock in the settlement. The risk to them is that at some point, Nino would have so much stock in my company that it wouldn’t be worth my time to continue doing the company. The investors want to make sure they don’t get involved in a situation like this.

So I assure the investors it won’t happen, but honestly, I have to work hard to make that true.

For the most part, divorce is a divide-down-the-middle thing. For an entrepreneur with a venture backed start-up, the trick is finding the middle. Because there’s no perfect way to figure out the value of the company. I try to make the company look valuable enough that I can pay off our debt and support the kids, but not so valuable that Nino thinks it’s his ticket to divorce heaven.

My lawyer, Allan, sees it as his job to put the fear of God in me: If I cash out big and it turns out I mislead people in the divorce proceeding, then Nino can come after me for everything. “Just be honest” is what Allan tells me. For $400 an hour.

I refer him to the blog post where I say that lying on one’s resume is an art form and honesty is not black and white.

He tells me that divorce law is different from career advice.

I say I think the difference is that career advice has more than a one-time use.

Allan thinks this is not true because he thinks that one day I will divorce the farmer. He says, “Your farmer has land in the middle of nowhere. If you like farmers, I have a farmer for you. He owns the land at the end of [sworn to secrecy — major road in Wisconsin]. And he just sold a bunch.”

I remind Allan about how pissed off he was when I wrote a post about the last guy he set me up with.

Allan concurs: I am a nightmare to set up on a date.

This conversation takes place on the short walk to the building to meet Nino and his lawyer.

Allan asks me how I’m feeling about custody.

This is why I like Allan. He cares about me. He is thinking of the flurry of phone calls I made to him after I read that women who make a lot of money are losing custody to their husbands who make no money.

“Where did you read that?” Allan asked.

“In the London Mail.”

Allan said, “Forget it. This is Madison. Don’t worry about it. If you want to know what to worry about, worry about the company.”

I didn’t know if I should believe Allan. I didn’t know if I should worry. I have so many mentors who help me with my start-up: almost all of them are men, and all are extremely generous with their time and ideas. But none has experience losing custody as a mom.

So I asked Nino one day, when it was our three-year-old’s birthday and I was premenstrual and I forgot half of the goodie bags, “Do you think we parent equally or do you think you do more?”

He said, “I think you do way more than I do.”

I said, “Really?” I should have recorded it or something. But instead, I cried.

He said, “Could we just have a normal birthday party? No crying?”

Okay. So, flash forward, to the meeting with our lawyers. And in our ongoing quest to be normal, Nino and I sit in the room and we try to do niceties. But niceties are difficult for me and Nino. Not because we are not nice to each other, but because we are bad with small talk. I feel an affinity to him when both of us are befuddled during lawyer small talk about the weather and the Badgers.

We get down to business. Which is the business of figuring out how much my business is worth.

Nino’s lawyer, Steve, is worried that my business is stupid and I’ll never be able to pay off our debt. He says, “So much of the business is you. What if people start saying bad things about you?”

I say, “Haven’t you been reading my blog?”

Nino says, “No. I told him not to. I thought it would be too expensive.”

Steve says, “I’ve looked at it.”

I say, “Did you like it?”

Steve smiles. Or maybe he says yes. I can’t remember. But I remember getting the distinct feeling that he would let me use his name in my blog posts even though Allan told me to never use Steve’s name.

Me: Didn’t you see the comments? People tell me I’m an idiot all the time.

Steve: Well. I didn’t see that. But I saw the letter to the editor in the Wisconsin State Journal.

Allan: I have it right here.

Me: What? What is that? A scrapbook?

Allan: Yeah. Sort of. Here is where you were covered in the New York Times. Steve, did you see this?

Steve: Oh. What is this?

Me: Let me see the letter to the editor. Oh, this is just some over-educated person from Madison whining about how her graduate degree mattered.

[I look up. The lawyers are lost in the clips. Nino is shaking his head incredulously. Then everyone looks up.]

Me: I get hundreds of comments each week saying how stupid I am.

Steven: Really? I think I don’t understand how the business works. I thought you were an authority.

Me: It’s a fine line, stupidity and authority.

Nino: [giddy at the line of questioning] Oh, do you think so?

Steven: Can you explain the company again? How do you tell investors that you are going to make money from this thing?

Me: Well, I think the way I explained it last time probably didn’t work for you. So, I have an idea. Would you like me to give you the pitch I give to investors?

Steve: Sure.

Me: Should I stand? I usually stand.

Steve: Okay.

Me: Well, I usually have a PowerPoint presentation as well.

Allan: We can imagine it.

Allan is excited that I’m going to do the pitch. He thinks our best-case scenario is if Nino and his lawyer understand the company very clearly. Allan says they’ll leave all the stock to me if they see it’s in everyone’s best interest.

So it turns out that the key to a good divorce is good communication. Hilarious. For people who are not us.

I look over at Nino. He’s never even asked me what my company does. I am secretly happy to finally tell him. I think he should be more curious.

I do the pitch. At first I sort of tone it down, but then I get rolling. I realize that I don’t need the PowerPoint. I say, “We aggregate people who blog about their careers.” Then I talk about how great the bloggers on our network are: “Super-engaged employees that employers are looking for.” I toss around some financial estimates and explain, “We encourage employers to recruit by having a conversation in the blogosphere.”

Steve says he thinks that companies don’t know what blogs are.

Steve says he doesn’t see an employee shortage in Madison law firms.

These are not good observations. I worry that I have not explained things well.

But then Nino says, “That stuff is not going to be a problem. The problem is that the PR people won’t want to let everyone talk to bloggers.”

I say, “Nino’s right. That’s the weak link in the plan. He’s so smart. That’s why I married him.”

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  1. prklypr
    prklypr says:

    Wow! This is brave! I admire you – when you say you are going to blog about work and life, you really do it! This post describes the ultimate intersection of work and life. Your lawyer will hate it. More power to you.

  2. Sara O.
    Sara O. says:

    I think your advice is wonderful and it has helped me tremendously. It’s honest and realistic. This world doesn’t need anymore bullshit flowery pats on the back.

  3. Dave
    Dave says:

    I can’t help but notice the dichotomy between this post and your recent one about salary transparency.

    (I was going to write more, but I kept thinking about your excellent recent post on mentoring and the advice about keeping things on point – see, I’m not just a hater!)

  4. Mike
    Mike says:

    “honesty is not black and white.”

    With a worldview like this, you are your own worst enemy. Truth is not a subjective construct.

  5. Susan
    Susan says:

    Penelope, this dialogue would make a great episode for a sitcom. But you’ve probably thought of that already.

    To your point about PR people, I get at least a dozen unsolicited pitches from PR people per week. Some of them want coverage mainstream pubs that I write for, but others specifically ask for coverage in my blog. Smart PR people are wising up to the power of blogs. Heck, many of them are blogging themselves!

  6. Angry Receptionist
    Angry Receptionist says:

    Mike, have you ever done anything wrong? Do you wear a sandwich board advertising it because honesty is black and white.

    Oh….right. Truth is black and white, but honesty, or when to divulge things, is complicated. Do you tell a first date that you have AIDS? Do you tell the cop that pulled you over that you’ve been arrested before? Do you tell your boss that you’re reading this blog instead of working?

  7. James
    James says:

    I don’t mean to be a jerk, but your “company” has a 117,000 Alexa rank. That’s what we in the industry call a joke.

  8. Dan Schawbel
    Dan Schawbel says:

    I think it’s 70% of the Inc. 500 have blogs and 25% of Fortune 500 have blogs. Basically, companies know what blogging is, they just don’t know how to monitor it, use it for decision making and take action. I know this because I work for one in the 25%.

    My blog got me my job, but I’m not sure how it helps me keep it. PR People are obsessed with bloggers now, as I receive many press releases each day that I label as spam.

    There is such as an amazing opportunity to embrace much of what Penelope mentions in this post, but the problem most companies have is that they don’t know how to grade it as “proficiency” and put it in our “job descriptions.”

    This is part of the battle I’ve been fighting.

    Cheers to a good weekend.

    – Dan

  9. Anna
    Anna says:

    How interesting. A discussion about properly allocating the company in the settlement, and your husband didn’t know what the company did. I enjoy your insight and exposition as your divorce unfolds (as I enjoy every peek into a blogger’s persona outside of the theoretical).

    I wish you luck in working things out with Nino.

  10. Joselle Palacios
    Joselle Palacios says:

    My selfish wish is for you to sell the company and write more books. You seamlessly went from hilarious to very touching and bittersweet. I love that you write being nice isn’t hard; it’s small talk. I relate.

  11. Patrick
    Patrick says:


    I love your reasoning.

    It’s the same logic that gets us craptastic television and even more vomitous music.

    Traffic trumps merit, so instead of anyone who can sing, or dance, or has even a modicum of talent, we have Britney Spears, a person whose main talent appear to be forgetting to wear undergarments in public.

    Merit trumps popularity every day in my book.

  12. oldcurmudgeon
    oldcurmudgeon says:

    Good luck to you and Nino in sorting this out without shifting all your wealth to the lawyers. There are a lot of terrible things about divorce. One of them is that divorce is a great way to go from financially comfortable to financially strapped in a hurry.

  13. Maggie
    Maggie says:

    I so envy you that your divorce seems so amicable with regard to the custody issue. Mine was a nightmare and since I didn’t want to drag my kids through the custody battle that my ex’s cutthroat lawyer convinced him he wanted my kids only sleep at my house 50% of the time. I am lucky in that I see them almost every day and live 5 minutes from the ex’s house, but I still have access to his house and it is absolutely disgusting and there’s nothing I can do about it.

    Divorce sucks but at least it sounds like neither of you has the kind of lawyer my ex did–the kind who wants to make as much money as possible so escalates things to his advantage. Our divorce started as mediation–was totally amicable and was going to be cheap–then his parents got him this lawyer and it ended up costing me, all told, probably $50k. All to arrive back at what we had originally agreed on!

    I will say, though, that your post makes me glad we didn’t have financial issues–I can only imagine what his laywer would have done if he smelled money!

    BTW, I admit I don’t understand how your company works either! You should post your presentation here because I am not an entrepreneur and have no idea how bringing together a bunch of bloggers equals big money.

  14. Aaron
    Aaron says:

    Patrick, Patrick, Patrick…sometimes, something is not popular because it sucks (or is a bad idea). And sometimes, some things are popular because they are excellent (not Britney of course). The current Batman movie is an example. Extremely popular but also well regarded critically (haven’t seen it, don’t have an opinion).

    Oh, and the number one ranked site on Alexa is Google which, if you are equating as the Britney Spears of websites (since its genesis is directly related to creation of a company worth tens of billions of dollars), is just plain ignorant.

  15. Greg Rollett
    Greg Rollett says:

    @james – since you’re in the industry you would know that Alexa is a joke. Remember that traffic is not king, conversions are.

    P keep rocking your crazy style.

  16. Mark W.
    Mark W. says:

    It sounds as though your presentation about your company was understood by Nino. Evidently his lawyer has limited understanding here or has further questions based on your observations. Maybe Nino can help out and bring him up to speed.

  17. Dan Owen
    Dan Owen says:

    You get one detail wrong, P. You’re not going to divorce the farmer. The farmer is going to divorce you.

  18. Marsha Keeffer
    Marsha Keeffer says:

    Now I more fully understand ‘all job search all the time’, thanks.

    Your model is happening day by day.

    I’m a PR person working for Rubicon Consulting, a strategy consultancy in Silicon Valley. Our CEO, Nilofer Merchant wants us to blog and write on the industry. It’s community and it’s how we connect with others in the world (and not just clients!).

    There are still a lot of ‘old school’ companies, but blogging and writing are moving toward becoming the norm, particularly in tech. No PR person is going to be able to stuff this genie back in the bottle – I certainly don’t want to.

    For companies that walk the walk, good news spreads far and fast. And if you say it online, you’d better also be living it or you’ll be caught out.

    I wish you and Nino a respectful divorce – I’m certain you can come to a fair agreement.

  19. Ann
    Ann says:

    Sorry, Penelope — well, Nino. I’ve been a fan and communicating with Nino occasionally since before the Bankrate Days. Yes, Ann from Career Development in Ohio.

    Having been a “victim” of divorce years ago, i could see the handwriting on the wall in NYC. Nino never got it together. You might have changed careers — and venues — but you were always smart about it. Nino sucked at be at a stay-at-home dad and sharing duties. If you want majority custody, then you deserve it. Your sons are lucky to have someone so invested in their complicated lives — and it isn’t easy!

    BTW, I wished I could have hired you as a speaker, but Ohio lost the funding for me to do so. And I missed the Madison conference. I hope to meet you sometime in the near future.

    You are an inspiration. Ann from K-12 Career Development in Ohio

  20. Caitlin
    Caitlin says:

    I hate to nitpick when this was not the point of your post, but this is really bugging me.

    It’s NOT the London Mail, no more than it’s the Birmingham, Manchester, Glasgow or Cardiff Mail. The title of the newspaper is the Daily Mail. If you need to be specific and it’s a common title so I guess you do, it’s the UK Daily Mail. It’s a national newspaper, not a city-based newspaper.

    You did this recently when you referred to The Guardian as well, calling it the ‘London Guardian’. Please don’t.

    I know that the US newspaper market is based around metropolitan brands – the New York Times, the Washington Post, the San Francisco Chronicle, the LA Times etc. That’s not the case in the UK, which is a national newspaper market. The Times, The Guardian, The Independent, The Daily Telegraph, The Daily Mail, The Daily Express, The Sun and The Daily Mail are all national newspapers and none of them are London newspaprs.

    London has four newspapers and most people outside the UK probably haven’t heard of them – the Evening Standard, the Metro, thelondonpaper, and the London Lite. The Standard is the only one that’s not a freesheet.

    The thing is that this is not a trivial point. It’s in accurate in fact – actually some of these newspapers historically had a base in other cities (the Guardian is from Manchester for example). But it’s actually also deeply insulting to the 50 million Britons living outside London every time one of their national institutions is described as a London one. The UK is already London-centric enough on its own without outsiders helping that process along.

  21. Adunate Word & Design
    Adunate Word & Design says:

    Caitlin, very interesting post! And helpful correction, as we in the U.S. would otherwise have no clue.

    This is why I read Penelope Trunk, who like the Daily Mail, cannot be labeled the Madison Trunk. She’s international. She and her readers take me beyond my little Midwestern town and show me the world.

  22. chris
    chris says:

    I am in the medical profession, which is really old-school, and I cannot imagine using PTs model in medicine.

    I think the lynchpin of this model must be writing. Blogging is mainly writing, showing one’s super-engagement through writing; showing one’s communications talents through writing. Yes?

    Marsha helped me understand this–I needed her feedback to PTs original entry, in order to get it. Therefore, PT, I think you SHOULD make your presentation in an expanded and clarified format.
    Your conception of the networking seems creative to me, insofar as I understand it. Please say more. Thanks.

    As far as the divorce is concerned, you brought up a gazillion divorce issues. I lost focus after I felt reassured that YOU would have custody of your kids. That is primo for me.

    You have blogged recently about the discipline and frugality of writing–its laser quality. (This blog entry was all-over-the-place, however. That is not to say I didn’t enjoy this entry.)
    You now talk about honesty in communication, and how non-black/white it can be. If that is true, you must aim for clarity, if not for black-and-white honesty.

    Last, I profoundly respect and admire your ability to accept and use critism (and deal it out, as well).


  23. oldcurmudgeon
    oldcurmudgeon says:

    The blogging software seems to have eaten most of my prior comment.

    You do not need to set a value for the company. Your investors have done that.

    The valuation for divorce purposes should be the same as for fundraising; otherwise, you have a problem that won’t go away. If the valuations are different, either the investors or your husband have a claim they’ve been had.

  24. Don B.
    Don B. says:

    I agree with Maggie and would like to hear how your company works on a post sometime. And thankyou Caitlin for the UK newspaper information. I am not sure what to do with that information but always liked thorough specificity. I wish divorces weren’t so obsessed with financial division. Thanks for sharing. As far as the people who choose to label you with derision I say: a person who does not stand for something will fall for anything.

  25. Quasar9
    Quasar9 says:

    I meant how much would it cost you to nuy out Nino’s half
    e-mail me a ball park figure.

    I think I’d be quite into having you as a partner right down the middle – as long as there are no dividing lines in the big brass bed.

  26. Nino
    Nino says:

    Wow. Now the commenters are trashing me too! I should be getting paid for this.

    @Ann from Ohio: You think you might not be hearing the entire story?

  27. Ann
    Ann says:


    I’ve been reading Penelope’s blog since way before Bankrate. Maybe 8 years or so? If there was a problem with the story, wouldn’t you have corrected it before you were getting a divorce? Maybe you should have been taking career advice instead of changing careers so often.

  28. Andrea
    Andrea says:

    “I look over at Nino. He's never even asked me what my company does. I am secretly happy to finally tell him. I think he should be more curious.”

    Heheh. I get this.

  29. sophie
    sophie says:

    A wise mentor said this, “There are two sides to every pancake, no matter how thin the batter.”

    That said, I do agree with the comments above that divorce is expensive. Not that I’ve traveled that road. But my many close acquaintances who did divorce all created the same scenarios for me, the outside observer to note.

    #1. Both parties get so emotionally wrapped up in what’s happening, they can’t see beyond themselves and their own viewpoints. They both completely believe they are in the right.

    #2. There’s no such thing as an amicable divorce. Even the best intentions get nasty. You can’t do it without a lawyer. You can’t do it with a lawyer. See above.

    #3. Divorce takes years and years to recover from, both emotionally and financially. All my acquaintances went through about 5+ years of great financial difficulties after the divorce. See the above two points.

    #4. Divorce affects the kids. The parents can’t see it because they’re so involved in the issue. But an outside observer can see the kids stuck in the middle, watching, listening, scared. The kids take it personally. They act out in any number of ways. They carry the emotions with them for years and years. What makes it most unfair is, they have no say in any of what goes on, yet it affects them equally as much. See above three points.

    #5 More than one of my acquaintances said, in retrospect, that they divorced too soon. They wished they would’ve tried harder to work it out. See all of the above.

  30. Oldcurmudgeon
    Oldcurmudgeon says:

    Ann –
    Reading the blog doesn’t mean you know either Penelope or Nino, and you are way out of line settling his hash here.

    There are Always two sides to a story.

    Penelope, a natural marketer, can be counted on to put forth not a neutral view or both views but rather the defensible version that best serves her interests. There are a multitude of very good reasons for Nino not to take on the task of setting out his quibbles and disagreements in the comment section for your amusement.

    This story is sad enough already. No one in the marriage gets helped when some oafish stranger with a bogus sense if personal involvement (that would be you) decides to mean spiritedly attack the spouse. Let them be, and hope emotions remain calm enough that they can eke out the best solution still possible.

  31. Joel
    Joel says:

    Pathetic really. I want to hear Nino’s version — I’m sure it would be closer to the truth. . .

  32. Leanne
    Leanne says:

    Penelope would you give us a virtual pitch about your company – blog it so we can be advocates – who knows you might even snare an investor … there sounds like a few keen bodies in the comments above.

    Maybe you have already written it and I have just missed it … point me in the right direction if that is the case. Cheers for now

  33. John
    John says:

    I really don’t understand what it is that you do. You blog about nonsense, and you get paid for it? You try to make a crappy job situation look positive…You want to start a company as a b.s. blogger? We live in a crazy world, don’t we? how much time did you spend raising your kids if you were constantly blogging? I wonder…Maybe the need to blog about your personal life is some kind of yet to be diagnosed sickness. People wonder why our young people are so messed up….

  34. Ellen Hart
    Ellen Hart says:

    As always, your posts are insightful and entertaining. I hope everyone in the room got a chuckle over your comment, "That's why I married him."

  35. Ann
    Ann says:

    Old Curmudgeon certainly fits you and your style of writing. Obviously, you didn’t read both my posts. Reread yours also before you post. (see blogging 101) Enough said. Nino has the right to his own blog, which he doesn’t have.

  36. Yu Ming Lui
    Yu Ming Lui says:

    Divorce is tricky but it seems you got yourself a great lawyer.

    Your blog is fascinating – how you always illustrate real work-life balance challenges and realities. Women can’t have it all and yours is a down-to-earth take on this topic.

  37. Smith+Fritzy
    Smith+Fritzy says:

    I’m amazed by the comments here. Most of you speak as if you’re really in her shoes – which I guess means she’s doing a good job in her writing. But one of the reasons Penelope does well in her blogging is because she’s a good storyteller. Not everyone can keep an audience reading or listening the way she does. She’s a career/business strategist/adviser and she’s writing her messages through story versus hitting you over the head with it. When you read her post, each of you got something different from it. It made you think critically about situations you’re in or could be in and think about how you would handle them. And just to leave off, just because she gives us a little opening into her life doesn’t mean we have a clue what’s really going on with her or the other parties and you’re missing the point of the post entirely.

  38. J
    J says:

    Ann, Oldcurmodgeon has a point. You do sound rather silly. If you have to remind Penelope 2-3 times of where you are from, and you allude to the fact that you’ve never met, how can you feel comfortable speaking about her marriage like you are a personal friend? Okay, you’ve communicated to her about it…that still doesn’t put you in a position to presume that you can tell Nino about himself. If you and P are so tight, email or call her. You just sound a bit off.

  39. IRG
    IRG says:

    Just because blogs exist does not mean everything should be blogged.

    And that’s got nothing to do with whether one is Gen X, Y, or whatever. Age is not the issue. Discretion and common-sense are the issues. (Personally, I feel Penelope lacks these in this situation and many others.)

    Penelope blogs, it seems, because she likes not only the “sound” of her own voice and thoughts but also because she loves the attention she gets. (She wouldn’t be the only blogger to fit that bill. It’s as if just because someone wants to blog, they believe what they say is worth the world’s attention. NOT!)

    Anyone who would share so much of her divorce (which is private and between two people and their families) in public, is clearly putting herself and her interests first. Not her kids, that’s for sure. Airing such matters is totally selfish on her part. It’s as if she has to make her case publicly to get validated.

    She can make all the excuses, rationalizations, whatever she wants, but for anyone who has gone through a divorce, publicly airing your private stuff…NOT a good thing for anyone.

    No matter the circumstances.

    P is commercializing her divorce. What does that say about her, personally and professionally?

    All of life is NOT fodder for your work, Penelope. Some day, you may grow up and realize that.

    A lot of people write about their feelings to work through stuff. The mature ones just don’t publish it for the general public.

    Any credibility you may have had has been diminished by your constant insistence on airing your private life. And bashing others publicly.

    If you can’t “edit” yourself on something like your private life, one truly doubts that you can edit yourself (in a positive sense) in business.
    Which makes your professional credibility questionable.

    Stick to writing about work issues. And get some help (therapy) to deal with your personal issues. You really need it. You may be a good mother, but you are giving a poor example to your children.

  40. Phil
    Phil says:

    Print out all the blogs and you should have no issues getting what you want in the divorce. Your character has been continually defamed, there have been allusions to infidelity on her part, she has changed jobs plenty, etc. Any judge who is showed a ‘sampling’ will have no issue siding with the sane one of the bunch. Just be sure to put all her aliases down on your petition as you don’t want her to ‘win’ because you used the incorrect name in the divorce petition.

  41. Dale
    Dale says:


    A divorce settlement is like a get out of jail card. It may cost you alot, but it ultimately gives you your freedom.
    The only question is can you live with yourself after giving up what you had to give up for that freedom?

    That’s what lawyers are for but as with medical matters, be totally involved in the process, and don’t be afraid to give a “little” more than others may advise, if only to ensure amicable relations – you’re in each other’s lives for the lives of your children. Take the high road.


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