Assess yourself: Should you launch a startup?

I fired Melissa.

We were bickering all the time. And she was saying I’m impossible to work for and I was saying she’s impossible to manage. The problem is I’m a mad raving lunatic about making sure that people who work for me like working for me.

When Ian, the guy who I was going to do a company with but then ended up not doing a company with, asked Ryan Healy and Ryan Paugh for references for me, they said I was loyal and caring and they both gave me so much credit for helping their careers and it just made me really really happy. I want to know I am making peoples’ lives better.

So when I told Melissa I was going to launch a company, she asked what her job would be, and I said, “Nothing. You are not in my company.”

If you’re wondering if you’re going to be a good startup founder, ask yourself if you are able to fire friends.

Right now most of you are thinking, “Oh. Then I couldn’t do it.” But some of you are big enough jerks to be startup founders, so here are more things you need to have up your sleeve:

1. Ability to make difficult decisions quickly.
I couldn’t totally fire her because she does an amazing job with the photos on this blog. So I fired her from everything besides that.

I am largely heartless about firing people, which is why I’m a good startup founder, so I just moved on, right away.

I didn’t know Melissa was crying.

2. Ability to put together scrappy solutions to big problems.
So when I asked her for the login information for the Start Your Own Company webinar, she ignored me. That was a problem because tons of people have been buying the on-demand version and for a few days there, I couldn’t find it. But eventually I got most of the information I needed.

Then I went to New York to lock down funding for my startup, and Melissa moved to New York because her laid-back Austin boyfriend suddenly became her high-flying financial industry New York boyfriend.

I brought her flowers. Hydrangea.

She said, “What is this?”

“It’s a housewarming present. And a let’s-be-friends present.”

“That is so awkward.”

“Why? Don’t you like the flowers?”

“No. I don’t want to be your friend. You don’t have any friends. You just have people you work with, so I want to work with you because I love being part of your life.”

I said no. I held firm. I am not having people who don’t like working for me working for me.

Melissa pushed until I apologized for being rude and inconsiderate and then before I knew it, we were shopping for an outfit for me to wear to meet the investors.

Which is good, because who knows how I would have picked one by myself?

3. Ability to sell an crazy idea to a cynical audience.
I got funding. I am a rock star, okay? I funded my company with two phone calls and two meetings.

Okay. Well, you could say it that way, or, you could say that I have actually launched three companies in the past three years that sucked and were unfundable and died the day I showed someone the deck.

The moral here is that if you have a good startup idea, it gets funded.

4. Ability to handle financial insecurity.
The farm bank account has been funding the company, but Matthew has to buy cattle and we are approaching a disaster because I did things like buy a domain name instead of pay my phone bill. (And like ten other bills too because domain names are not cheap.)

So the day after my meetings where I am dressed very well I tell Melissa I can’t hang out with her because I need to open a bank account so the investors can wire the money so that I do not fall into financial ruin.

But it was too late for that.

5. Ability to recognize a good hire and a bad hire.
Melissa decided to tag along on the trip to the bank.

We get to the bank and I can’t open an account because I don’t have a New York address. So she gives me hers. Then I can’t open an account because I don’t have a $100 check to deposit into the account. So Melissa writes a check. And then, it turns out I cannot open a bank account because my other account at Wells Fargo is overdrawn.

So Melissa is not fired anymore. Instead she is opening my company’s new bank account. And I am documenting it.

6. Ability to be transparent in order to instill trust.
The bank guy, who told us 400 times please do not use his name on my blog, said that it looks like I work for Melissa now.

Melissa said, “Yeah. It’s my company. And you’re fired.”

I tell the bank guy we are in a rush and he needs to open another teller window or something.

Melissa tells me to shut up.

I tell him I meant it in a nice way.

I take his picture but he ducks.

I say, “Don’t you want to be on my blog?”

He says, “I think the Internet today is often demeaning of our privacy.”

Melissa says, “Penelope doesn’t do privacy. Well, she does. She sells her own. And mine.”

That pretty much ruined any chance of me getting his picture. But you’ll have to just trust me that he was very excited to be helping us launch my company.

7. Ability to experience wild mood swings.
I decide I will do work while Melissa opens my account. And then I drop all my stuff on the floor. And then I am losing my phone and I am yelling to her from under the desk that I can’t find my phone and she is taking pictures of me using my phone.

I love Melissa for caring so much about me that she’s taking pictures and opening a bank account. I want to hug her, but she’s the size of a seven-year-old girl, so it’s better to just do intellectual banter with her. And to her, that’s like a hug.

While we wait in the bank guy’s office Melissa tells me it’s frustrating that I either love her or I’m screaming at her. I tell her it’s how I’m supposed to be. I search my phone for this link about entrepreneurship.

“Look, read this. It’s a present for you,” I tell her. She reads. The money quote is “People who are on the energetic, motivated, and creative side are both more likely to be entrepreneurial and more likely to have strong emotional states. Those states may include depression, despair, hopelessness, worthlessness, loss of motivation, and suicidal thinking.”

She says, “This is a present for you, not me. You think this justifies your erratic behavior.”

“Hm. You’re right. And I think it lets you know why you are so lucky to be a part of it.”

I show the article to the bank guy. He is our friend now. “Would you ever do a startup?” I ask him.

Melissa says, “Of course he wouldn’t do that. He’s too nice. He is pleasant. He has social skills.”

He does not know if this is a compliment or an insult, but in any case, he says the account is done. The wire transfer will be available in an hour.

We go out to lunch to celebrate the new company.

I still have no money, so Melissa pays, and I take a picture.


64 replies
Newer Comments »
  1. Kathy Donchak
    Kathy Donchak says:

    I love the transparency of your blog, good or bad you can learn something with every post. The world is not a perfect place and life is messy – if you are willing to go get yours! Cheers on your new company!

  2. PatriciaRossi
    PatriciaRossi says:

    THis was a wild ride…
    Would have buckled my seat belt, but my desk chair doesn’t sport one.
    I know so many things come together in this manner, but folks don’t share this truth… and we continue to believe it’s an all buttoned up ,tidy, and perfect…venture.
    Courage ….. can’t be bound up…
    Thanks for sharing……

  3. Ann Marie
    Ann Marie says:

    I was sick to my stomach, when I read that you fired Melissa. Thank goodness, you came to your senses! Melissa is not a “yes” person; she truly cares about you, so she is honest with you. No one is happy with another person all of the time.

    Melissa should remain a part of the new business. She possesses many skills that you lack and as a result she bumps up your business game considerably, when you REALLY LISTEN to her.

  4. Karo
    Karo says:

    Love Penelope’s writing but this post blew it out of the ball park. Being an entrepreneur, I think that Penelope and I have been separated at birth. I will show this post to my husband who criticizes me for not being Mother Theresa of Business. lol

  5. Grace Miles
    Grace Miles says:

    I’m glad you and Melissa are still working together!

    And you know how I take sneak shots? I hold my phone in my hand and I don’t look at it while pressing the button. People only know you’re taking photos when you’re holding your phone AND you’re looking at it.

    (Don’t worry, I only do this for street photos– I’m not some creeper.)

  6. Priscilla Wood
    Priscilla Wood says:

    What I really would like to see is you in one of those meetings.

    I took your seminar, you were very entertaining and blunt, love it.

    I wonder if there are two Penelopes, one for seminar/blog and one for these business meetings or you’re just yourself all the time?

    I have no social skills and I tend to be blunt, so it’s extremely hard for me to know how to behave depending on social situations.

    • Penelope Trunk
      Penelope Trunk says:

      People tell me that I’m exactly the same wherever I go. Which is maybe evidence that we can all be ourselves wherever we go – we don’t need to adjust that much because people are more accepting than we assume they are.

      This is actually what I felt like when Melissa was getting me a bank account. I thought: the world is so forgiving and that is so nice.


  7. Gary
    Gary says:

    I really have nothing to say, but… Wow. Your power of persuasion is your superpower. You’re sort of turning Melissa into a rock star now, and I’m sure she knows it. Good luck with your new company. ☯

  8. Jen
    Jen says:

    I think being your friend must require a high tolerance for drama. But embracing crazy probably makes it all worthwhile in the end.

  9. Susan Overbey
    Susan Overbey says:

    Launch a start-up? I can’t even launch a blog! Don’t need money — need someone to create the bleeping web site!

    Trusted people to whom you can delegate are priceless. Sounds like Melissa is one of those.

  10. MBL
    MBL says:

    Holy smokes I need a nap!

    I read the “present to Melissa” link and found it interesting. I was particularly struck by:

    Though driven and innovative, hypomanics are at much higher risk for depression than the general population, notes Gartner. Failure can spark these depressive episodes, of course, but so can anything that slows a hypomanic’s momentum. “They’re like border collies–they have to run,” says Gartner. “If you keep them inside, they chew up the furniture. They go crazy; they just pace around. That’s what hypomanics do. They need to be busy, active, overworking.”

    Love the border collie reference.

    While much of the article discusses situational depression, there also seems to be a predisposition for existential depression in big thinker types. I’m totally on a James T. Webb kick right now. He just published a long awaited book Searching for Meaning: Idealism, Bright Minds, Disillusionment, and Hope. It is really helpful. Kind of a fleshing out of his seminar on existential depression that really resonated with me last year. I ordered the book directly from the publisher, great potential press, but it will be available elsewhere next month. Highly recommend!!

    Hydrangeas! Lovely! Especially periwinkle and chartreuse.

  11. Mary
    Mary says:

    Melissa has great eyebrows. Melissa, if you read this comment, please tell me how you do your eyebrows. Otherwise, this is a great post!

    • Melissa
      Melissa says:

      Thank you, Mary!

      I’d like to say I work really hard on them, but mostly I work really hard at not working really hard on them. (Other than that, sometimes I’ll fill them in a little bit with a cheap eyebrow pencil from the drugstore.)

      Annie over at xoVain gives a much better version of this answer here:

      PS: I pretty much just love everything by Annie. After I discovered her on xoVain, I went through their entire site and read every single article she’s ever written for them.


      • Penelope Trunk
        Penelope Trunk says:

        I need to comment here as well. When I saw Melissa, after the hydrangeas but before the bank, I said, “Oh my god, your eyebrows are so good, and I just got mine done and they don’t look as good as yours.”

        And Melissa said, “Yeah, you’re right. They don’t look as good as mine.”

        And I made her tell me, on a scale of one to ten, what are my eyebrows. And she said they are a six. So that’s why, on the last picture in the post, her eyebrows are front and center and mine are cut off.


        • Naomi Walsh
          Naomi Walsh says:

          You are hilarious. I just stumbled upon you today. I have never followed a blogger before. You are my first. I love your honesty and wit.
          I found you by searching for ” how to have positive thoughts in a negative world” and ended up reading an article on, 4 Rules High Achievers Never Break. There was a link to your blog. 3 Rules High Achievers Never Break.

  12. me
    me says:

    What ?! What happened to the plan to work with Ian??! I LOVED that guy.

    You two wouldve made a good team. Are you sure you cant resurrect him & bring him into the company like you did w/ Melissa ?

  13. robin kidder
    robin kidder says:

    Love this post. In my experience getting fired from the wrong job is the best thing that can happen.

  14. Cassandra
    Cassandra says:

    My heart sank when I read that you fired Melissa. Don’t you remember telling us about your untidy life? You concluded:

    “I am still that girl who wants a friend, and a job, and a place that feels safe. That’s my story.”

    I didn’t comment on the untidy life post but it was a beautiful, piece of writing & heartbreaking to read. Next time you want to fire Melissa – don’t! Remember your story (see above).

  15. Leah McClellan
    Leah McClellan says:

    This is so funny. It makes me wonder (as I have before) what it’s like in Melissa’s shoes. I mean, I wonder how it would go if I were working with you. I want to say it would be great because you cut through all the BS (seems to me) which is the way I am. But you’re kinda like me on steroids :D And I probably wouldn’t get along with me very well!

    Best of everything for the new business!

  16. Katie
    Katie says:

    Penelope after taking your last seminar it was so clear how valuable Melissa is for you. Your sharp edges are smoothed by her soft ones. Your big bright shiny lights are supported by Melissa. You get to be the rock star because you are so well supported by Melissa. You are an amazing writer but admit that you are kind of crazy. ( much like the rest of us a d especially me) but my point is that we need people like Melissa in our lives to tell us when we have food in our teeth and to save our asses when we f up and to let us cry to them when we feel insecure and exhausted. Melissa is all that for you and it is not something that should be taken for granted. We don’t get that many people in the world who love us so much as she loves you. In the end that’s all that matters.

    • Penelope Trunk
      Penelope Trunk says:

      This is such a lovely description of Melissa – she is so valuable to me. It’s hard to keep people around me who tell me I’m wrong, but I know I’d be such a loser if I couldn’t do that.


  17. Emily ENTP
    Emily ENTP says:

    That is an absolutely BEAUTIFUL picture of Z at the top!! If he were a hipster kid on facebook, it’d automatically become the best profile pic he’s ever had.

  18. Tracy
    Tracy says:

    So you showed up at her door, with flowers, apologized and then just ended-up shopping for a new outfit for the pitch. Start-up founder booty call :-).

  19. Chel
    Chel says:

    I really liked this post by the end. Great attention-grabbing opener, though depressing. Which brings me to the point.
    Lesson#8. Surround yourself with people who love you and are crazy enough to survive the roller coaster without losing their cool. ;)

  20. Carmen
    Carmen says:

    I’m requesting you write 2 more posts strictly for my benefit, because I think I need to know this:

    How to Find Your Own Melissa
    How to Be Someone’s Melissa

    Oh…another one…

    How to Know If You Need Your Own Melissa.

  21. Jo Ann den Hartog
    Jo Ann den Hartog says:

    Everybody’s reaction is oo-ing and aah-ing with anxiety and relief that Melissa was appreciated and saved. (As she has so obviously earned.)

    My reaction: I should definitely do a start-up.

    That’s scary.

    • Penelope Trunk
      Penelope Trunk says:

      That’s hilarious. You’re right, Jo Ann – if that’s your reaction then you should do a startup. And it turns out that this IS a good way to assess yourself, just not quite in the way I anticipated.


  22. Eve
    Eve says:

    I love it how Melissa, knowingly, made herself indispensable and got what she wanted. Which was to work with you to be part of your life.

  23. Nadia
    Nadia says:

    I think this is my FAVORITE post ever. Yes, yes, yes to:

    “People who are on the energetic, motivated, and creative side are both more likely to be entrepreneurial and more likely to have strong emotional states. Those states may include depression, despair, hopelessness, worthlessness, loss of motivation, and suicidal thinking.”

    This is very hopeful for me, thank you.

  24. Sarah K.
    Sarah K. says:

    I highly doubt you’ll understand this, Penelope…but somebody on here HAS to be thinking it, so I’ll say it…ever see House, M.D. while it was still on? Well, quite frankly, you are House and Melissa is Wilson.

  25. mbl
    mbl says:

    PT, if you don’t have the new Psychology Today, get it. Totally subscription-worthy. If Melissa decides to ration your link allotment, PT (the magazine) will have you covered.

    Interview with Hanya Yanagihara, author of The People in the Trees (which sounds fantastic.) She appears to be a major thinker worth watching.

    Article on Daniel Mark Lewin, ex-counter-terrorist Sayeret Markal member/genius/internet algorithm guru who was most likely the first killed on Flight 11. The article gives an account of the life suck that a start-up entails. And is a darn riveting read.

    Haven’t read the article on Borderline Personality Disorder yet, but looks to be interesting.

    Be warned, it is likely to inspire a toppling to read stack.
    Why Smart People Hurt and Republic of Outsiders look good.
    On the plus side, they do a busy person’s salient points of 8 books. So there’s that.

  26. Mads Singers
    Mads Singers says:

    In the end of the day, real success requires that one do what one must – In the end it’s not just a question of many people being to nice, it’s also a question of many people not wanting what they are aiming for enough….

    I’m not saying people need to be unpleasantly direct/rude, however when people are giving it everything, to get where they want to go, many of the “sheep’s” tent to get offended, not actually by the words, but just as much by the fact that there are people out there “Doing IT”

    Awesome post though, as always the transparency leave amazing learning points… and really if you are in “start-up mode” if you eyebrows are a 1 or a 10 doesnt really matter, does it?

  27. rebecca@midcenturymodernremodel
    rebecca@midcenturymodernremodel says:

    So Melissa doe not like working for you…then why does she mind being fired? I would think it would be the money. And, you have said constantly that your friendships center around people you pay. This must come with a now written rule. They kind of have to pretend they like you.

  28. Daniel Mumby
    Daniel Mumby says:

    Penelope, before you fire Melissa, may I suggest 2 word?
    “Exit Ramp”.

    Think about how much the poor love has put up with -and you have to remeber that -at least technically- she is your first seed investor in new venture, by an hour & $100 dollars. ;-)

  29. Ade
    Ade says:

    I am sure one doesn’t have to be as crazy as you to launch a startup, but to be successful like you and get funding like you and have fun at it, you need to be somewhat crazy but not necessarily as fun to read! Loved the article. You are talented.

    • Akintola
      Akintola says:

      You’re right. Starting-up with such behavioural pattern might sound so crazy. But for raising funds it’s cool. Moreso, i would like to know you.

  30. lex
    lex says:

    Have you considered what the Ryans’ would have said about you had they been asked when they were in the thick of working with you? Or what Melissa is likely to think about working with you retrospectively? My point is, you push people to their limits, which can be painful, but like any exercise, is so appreciated from a safe distance after the fact.

  31. Another Melissa Groupie
    Another Melissa Groupie says:

    I definitely think P doesn’t even realize how much Melissa does for her, apart from her job “duties.” She is practically P’s parent–finding lost articles, finding lost passwords or addresses…

    That sounds like a mother of a 1st-grader while she is attempting to teach the child how to do it herself. Only problem is that P doesn’t seem to be picking up the “learning to do it herself” part. I’m surprised the bank manager/executive/whatever didn’t ask Melissa if she wanted her “daughter” P to be able to sign checks w/out a 2nd signature from Melissa (Mommy–the in charge, rational one who keeps track of everything)…

    Oh, Melissa is also a beautiful young lady–more photos of Melissa, please!

  32. Emma Mackenzie
    Emma Mackenzie says:

    This article had me hooked! It describes the nitty gritty responsibilities any successful entrepreneur/business owner needs to uphold whilst also adding in humor and real life experiences. The ability to make tough decisions quickly is essential and having the guts to fire a person you genuinely like is something any budding entrepreneur needs to be able to do. A great read.

  33. Ally Smith
    Ally Smith says:

    Wow… way to go for giving us a candid account of starting your own business. You make it sound thrilling and terrifying all at the same time (which I’m sure it is)! The main thing I got from this though is that if you have a great idea for a business, you can make it happen. Awesome advice!

  34. Carl Allen
    Carl Allen says:

    Penelope – very interesting article. The part on financial security is interesting. Launching a start-up (as you can verify 4x) has to be one of the most nervous times for any entrepreneur: typically you will have no products launched, no cash, no employees, no premises, suppliers, anything. Isn’t it easier and less risky to acquire an existing business that has all that and more, and negotiating a deal (easier than it sounds) without having to inject any personal cash either for the purchase or to fund working capital?

Newer Comments »

Comments are closed.