Tips for coping when your startup is out of cash

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My company is running out of money again. Well, really, it already happened. But it's happened so many times that I am sort of used to it. It’s a routine. You may recall that part of the routine is not paying my electric bill. But there is more.

1. Focus on something you can control.
You might have noticed that my blog posts are very frequent right now. It's a way to cope with the funding drama. I have so much control over my blog. And if I obsess over the traffic statistics then I have that crack-head feeling of immediate feedback, and it feels good, and even if half the people are telling me how much they hate me: Traffic is traffic.

Another part of the out-of-funding routine is fighting with Ryan. When I am totally focused on running the company, and I'm not worried about payroll, then things go smoothly and Ryan and I have great conversations about the future of social media and the future of resumes and where we fit.

When we run out of money, Ryan and I focus on our cycle of miscommunication: I say something rude that I don't know is rude. Ryan gets defensive because he isn't able to say, “That's rude. Please don't talk like that.” I have no idea why he is defensive, he just sounds like he's up in arms about nothing to me, because if I knew I had been rude in the first place, I would not have been, so of course I don't know. And when he is up in arms, I yell back. And then he says that I am impossible to deal with because I'm rude and I yell.

So we did that fight routine last week at least twice. I lost count. But I know that the first time, Ryan said, “You know what? Sometimes I hate you so much I have to restrain myself from punching you.”

My jaw dropped. I did not expect him to say that. And then I said, “I feel the same way about you.”

The second time, Ryan Paugh yelled out from his office, “Shut up! Both of you shut up!” And we did. (Though I think Ryan Paugh felt like it was hopeless that we might actually stop, so he took a walk to the coffee shop.)

2. Take time to talk about what’s still going well.
So today I sort of kept to myself except that I had to go meet a board member to talk about the funding. The board member, Erik, is so fun to visit because he has this huge, stable company, and this gorgeous lair where he has an office and a secretary and a shiny deep-brown meeting table that my papers slide across while we figure out how to keep my company running. Erik is a great board member for a lot of reasons, but maybe the most important is that he's so stable. Brazen Careerist needs a lot of things, but really, it needs stability.

But before I go into the board meeting, I remember that I have been named one of the top 30 women running Internet companies.

I call Ryan Healy. He says, “What is that site? I've never heard of them.”

I have not heard of them either. But the women on the list are amazing. Arianna Huffington, Caterina Fake, Michelle Malkin. I am happy to be there.

There is one more good thing about today. Flowers. Another bouquet. From a blog reader. I think he might be in love with me. But whatever. He leaves great comments, and now he sent flowers, and the flowers make me happy. They make me want to sit at my desk and write one more blog post.

3. Accept help, but continue to exhibit your strengths.
After my meeting, it's 2:30 p.m. — Violin time. I leave to do school pickup, and Business Week calls. It's a conundrum. Should I talk to Business Week and be late? Or should I risk that Business Week uses a different source because I was unavailable?

I take the call. I try to summarize all my ideas about intergenerational offices in five minutes, and I try to hide sort of out of the way of my son's view, but he sees me. The rest of the call is about me getting off the call.

I buy my son his favorite after-school snack: Gatorade and KitKats. I tell myself it's an example of optimistic spending that only a top-30 entrepreneur would do.

We go to the violin lesson and I want to tell you I love violin, but I don't. I love the idea of the Suzuki program for violin. It teaches self-discipline, and perseverance, and working well in a group. I love that my son is getting all this, and he's so proud and works so hard, and I love the teacher.

But look. I'm out of money in my company and that's really all I have to think about for the half-hour they practice for his group recital. I am getting anxious about maybe not getting funding and I'm biting my nails.

Not biting sort-of-casually biting. But biting like I would imagine a serial killer does when he is trying to distract himself from thinking about the badness. Like, biting with way too much enthusiasm. And on top of this, I really really like my son's violin teacher and I worry that she is going to see me biting like a crazy person and not want to be my son's teacher.

And then I don't have to worry about the biting anymore, because he is unfocused and too squirmy, so I scream at him: “Put the violin under your arm and take a bow!”

Has that ever been yelled at a child? It's not normal. I know. And I know he is just anxious for his recital. The violin teacher gets very nice after that. To compensate for me being a psycho: This is how we are a team.

There is an hour break before the dress rehearsal. We go to the bagel shop for a snack. I have already prepared myself mentally for this snack. Normally, if I am having a bad day, I will have four bagels. But then I would be fat. Really. Four bagels can do that to you. They are like sponges in your stomach. So I told myself no bagels. Not even one, which would be okay, if I could actually eat only one.

To cope, I check my email. There is a note about me talking to CBS. I call them while my son is in the bathroom. They want to do a story about how Gen Y and Gen X don't get along.

I tell the guy from CBS that I manage five people in their 20s and they would all be happy to talk about why I'm annoying. The CBS guy is shocked. I give him Ryan Healy's phone number. Things go very well, of course. I know what I can count on Ryan for.

4. Hold things together, of course. But be okay if you can’t.
After my son has eaten two bagels, he is not chatty. So I look through my purse for something to do. I find the form for signing him up for classes to help him stay organized. By the time I am done filling it out we are late for the rehearsal and he tells me that I am unorganized.

I help him get his recital clothes on in the bagel bathroom, and we are not the last people to arrive. We wait. I take my son to get his violin tuned and his teacher says, “Black bottom.”

I say, “Huh?” Then I say, “Oh. Shit. I can't believe it.”

There are 100 kids ready to play their violins and only one of those kids is wearing khaki bottoms: My son.

Luckily, the violin teacher reads my blog, so this is not a huge surprise to her. And we acknowledge that I do have a second chance to get it right since this is only the dress rehearsal.

I almost cry. But I tell myself that if I'm not going to cry about running out of money in two days, then I’m not going to cry about khaki pants. I tell myself to focus on being a top-30 entrepreneur: Success does not come in a linear fashion.

My son and I wait for the teacher to call his group. And I am trying hard to not get blood on his shirt. Because his shirt is actually the proper shirt to be wearing, and my fingers are actually bleeding from aggressive bites.

So I am really overwhelmed now, between the violins and the fashion faux-pas and the blood, and then an investor calls. Yes. In the middle of violin even though I am certain that every investor I talk to knows that I am with the kids in the afternoon because they all bitch about it in a subtle way like, “Oh, that's great,” with body language like, “She is fucked.”

So I ignore the investor’s call because on my death bed I don't want to remember the day I took a call during my kid's dress rehearsal.

The teacher calls groups to the stage by the piece of music they are playing: “Allegro! Gavotte! Song of the Wind!” It looks like The Price is Right for the cultural elite, and the kids are walking up, nodding to their teacher as they go.

Each kid has a teacher there, except for my son, who has two. Because this program is really about the parent teaching the child and the teacher teaching the parent and the child and parent bonding through music. And that ended for us the time I got so frustrated that I broke my son's bow. Well, actually, the fourth time. So now we have two teachers. And when investors want to know why my salary is not the same as all those god-forsaken 22-year-old guys that Y Combinator funds, I want to say, “You try running a startup and teaching your kid violin. Violin lessons cost way more when you are running a startup.”

Okay. So there are 100 kids together on the stage playing. And it's stunning to see.

For a minute I forget that I am running a company that is running out of money.

All the parents in the audience are motionless; those tiny violins all together sound like a chorus of angels.

My son comes back to me in the audience when he's done. I say, “I'm so proud of you for working so hard.”

He says, “Are you proud of me for playing perfect notes?”

I say, “No. You don't need to be perfect. You need to just keep trying every day to be your best. And you are doing that. You should be happy for yourself.”

And he says, “You are trying to be your best every day, too, Mommy. You don't need to have everything be right. You should be happy for yourself.”

I cry.

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    • Penelope Trunk
      Penelope Trunk says:

      It’s nice that you guys care so much. Thank you. You know what? I adore this blog. I love writing for it, and I love the comments section, and I love the people I meet through the blog. Every day I feel lucky that my blog is going so well. So all of you do that for me. Really. And thank you.


    • Brazen blogger
      Brazen blogger says:

      Penelope pays herself $250,000 a year and lives in Wisconsin. Somehow I think she will be just fine. If anything, we should chip in to get her a personal assistant and a financial planner. Or maybe a professional organizer.

      -BC blogger

  1. Sally
    Sally says:

    I cried too !
    A virtuoso piece that was as beautiful for us to read as it was for you to hear your son’s violin playing.
    Thank you for choosing blogging and not bageling as release. We can enjoy the blog, we get no benefit from bagels!

  2. Elisa
    Elisa says:

    I have had your blog on my reader ever since I started following the Brazen Careerist website, and I’ve got to admit the last month or so I haven’t been all that interested in your posts. I’ve read them cause, let’s be real, you are a brilliant writer and have a way of seeing the young professional world that pushes people outside their box to think about things. But I haven’t enjoyed it.

    Today, I read this post, and I remembered why I love reading your blog again. You made a niche in the blogging community being able to observe the young professional world, offer insightful business knowledge, and yet still maintain a piece of your writing that made your readers connect to YOU. No longer were you some over-reaching voice on CNN or Money, you were Penelope Trunk, a human who went thru the same things the rest of us do. It’s good to see a post like this that brings you back to that, though I’m deeply sorry that you had to experience this particular episode to do it.

  3. Jenn S.
    Jenn S. says:

    Joe’s right, Penelope. What can your loyal readers do to help Brazen? For all of the great posts and conversations here, I would gladly donate a little cash to the cause. And if there are other things your legions of readers can do, let us know. We’re listening.

    Beautiful post to start a Friday morning!

  4. Gerty
    Gerty says:

    Wow, what an amazing post.

    Your son is so beautiful for saying that to you at the end. Thank you for sharing a small insight of your relationship with him.

    As others have said please let us know what we can do to help.

  5. Jesper L Ottosen
    Jesper L Ottosen says:

    And he says, "You are trying to be your best every day, too, Penelope. You don't need to have everything be right. You should be happy for yourself."
    AMEN – Really, we all should!

  6. Stuart Foster
    Stuart Foster says:

    Wishing you good luck with the whole “running out of money” thing. I’ve been in that boat quite a few times lately…but somehow am always able to pull out something cool at the end (I haven’t resorted to selling my kidney (yet)).

    The funny thing about this story is that I have so been the kid in the Violin recital (albeit it was chorus…but that’s splitting hairs). Showing up with the wrong outfit and being relatively unprepared on a surface level. Here’s the thing: as long as you kick ass and have a good level of understanding from those involved you are golden. Khakis? Who cares. I just hope you son played a mean recital :).

  7. Maggie
    Maggie says:

    Penelope, I’m telling you–you need to not take your own advice and write a book. Look at Ayelet Waldman–her book “Bad Mother” is on the NYT bestseller list after one week. I haven’t read it yet but I’m sure she’s got nothing on you in terms of writing–she is, in fact, a lot like you. The whole reason her book is on the bestseller list is because she wrote an essay about how she loved her husband more than she loves her kids. Landed her on Oprah. You can write as well–or better than–her and you have the connections and know how to sell yourself. She even got to be in Obama’s poetry slam the other night.

    You could write a book about motherhood and every mom would buy it because people like to read books about women who are worse moms than they are because it makes them feel better about themselves. Then you could start a blog network for bad mom bloggers.

    I’m so not a business person but it seems like that would be a good money-maker; big companies would pay big money to advertise to moms.

    If it makes you feel any better, you’re a better mom than I am because I would never sign my kid up for voilin lessons because I would forget to make him practice and I hate sitting through recitals.

  8. Lane Ellen
    Lane Ellen says:

    Damn you. I told myself I wasn’t going to cry today.

    I really need your son to come over and say that to me today. But your blogpost will have to do.


  9. Shadab Malik
    Shadab Malik says:

    I have subscribed to your posts but still I cant keep myself coming back here and check for new posts even before the subscription copy falls into my mailbox.

    I ran out of money in October 2008 and had to shut down the company. I was far more disorganized than anyone else in the world. I hope this doesnt happen to you.

    All the best.

    And hey! Congrats on being among the TOP 30. How does it feel being there? :)

  10. Todd @ The Personal Finance Playbook
    Todd @ The Personal Finance Playbook says:

    This is the best blog I read. I’m glad you’re posting a lot right now. This post was one of your best in awhile. The whole thing made me want to cry, but especially your son. He sounds like a great kid.

    Good luck getting your investors lined up. Things will work out. Even if the company doesn’t work out in the long run, you’d have the Penelope Trunk brand to fall back on – and that has a great deal of value.

  11. Ryan
    Ryan says:


    This is brilliant. Authentic, vulnerable, and real. Please keep these stories coming on your startup progress. You’re telling such a great story here. I only hope you can cope with the anxiety and stress you seem to be having. Have you tried meditation?

    • Maria
      Maria says:

      I like the ending of your post. As a parent, I’m pretty sure that hearing those sweet words from your child can really uplift your spirit. I hope everything in your life will went well.

  12. Blondie
    Blondie says:

    I cry too, Penelope. I don’t even have kids, but I totally get that breathless, barely holding it together feeling that just seems to be life for people with jobs and families and the aspiration to “get it right.”

  13. Mark W.
    Mark W. says:

    I think you’re coping very well given all the start-up stress, fairly recent divorce, and responsibilities of being a good Mom. A lot of business and personal stress to say the least. Thank you for sharing your touching relationship with your son and his violin lessons even if a bow or two is broken is the process. While your son may point out you are not organized, your priorities regarding time spent with your children vs. taking an investor call during a violin rehearsal or whatever are spot on. I think he’s acquiring your good humor and both of you make a good team.
    I especially liked the last few sentences of this post and most notably – “I say, "No. You don't need to be perfect. You need to just keep trying every day to be your best. And you are doing that. You should be happy for yourself." because it reminded me of what my parents told me and what I think is the ‘perfect’ answer.
    I also think you have an amazing network of co-workers, friends, mentors, and supporters that will see you and your startup through this current dilemma of cash flow. My advice – use them and accept their help where it makes sense. You’ll probably experience some more nail biting episodes but you’ll get through it because you are resilient.

  14. KateNonymous
    KateNonymous says:

    This is the first post about your work-life issues that has made me feel sympathetic to you. The life part, that is. I would never want to work for or with you.

    It’s clear that you’re overwhelmed, and that’s because you’re doing too much. Some of that cannot be avoided. But some of it can. A lot of this is your choice, so continuing to be overwhelmed is also your choice. (Are you sure this is the right time for a startup like this, for example? I mean, the right time for you?)

    Your son sounds lovely. Congratulations.

  15. prklypr
    prklypr says:

    You should take the time to listen to your son more often. Kids find the inner beauty in everything.

    • Lois Swinburne
      Lois Swinburne says:

      My husband recently came home from work and the kids were going crazy. Eventually they got told off. My eldest, only 4, was upset. He explained to my husband that they were only excited because ‘you’re always at work daddy and we never see you. Thats why we are so excited’. It broke his heart. ALWAYS make time for your children. The time never comes back. Sometimes this is difficult but you have to make the effort.

  16. Melanie
    Melanie says:

    Your son is so insightful because he’s learned it from you! In the interest of some sort of pep talk, the big picture is that your son sounds like he’s growing up to be a wonderful and insightful person and that’s because of you!
    And if that tidbit didnt help, I know I’ve atleast contributed to your traffic stats!
    All the best!

  17. Natalie
    Natalie says:

    I’ve enjoyed your more frequent posting schedule and I really appreciate your honesty about this issue. I look forward to hearing about how you come through this latest challenge.

  18. Susan
    Susan says:

    It was touching. Your is indeed amazing.


    Why do you keep doing this to yourself? Why did you intentionally choose to create a work environment that would be so unstable financially and emotionally? Something is going to blow up in your face, more than just khaki pants.

    • Penelope Trunk
      Penelope Trunk says:

      Benefits to having my job:

      1. I make my own hours.

      2. I can be with my kids as much as I want to. I pick my kids up most days. I’m home for dinner most days.

      3. I choose who I work with.

      4. I meet really interesting people all the time.

      5. I get to focus on ideas, trends, strategy and writing. All things I love.

      I could get another job pretty easily. This is the one I choose. Each day.

      If I wrote about how much I love my life, no one would believe me. People do not love or not love their life. Life is hard for everyone. We keep getting up each morning because we love the challenges of life.

      We all try to create a life that is good for us. There are no right answers. Only honest discussions.


  19. Anne
    Anne says:

    What your son said was so sweet that I teared up a little. That is really just precious. Good luck!

  20. ioana
    ioana says:

    Okay, do me a favour, put a donate button on your main page. Min. donation 1$. Paypal. So you can keep blogging.

    (sorry didn’t get to read the whole post yet, my job just went crazy)

  21. Erica
    Erica says:

    My mom broke a number of my bows when I was learning with the Suzuki method. One bow she broke by hitting me with it. Suzuki is really hard on the mother, I think. You have all this responsibility, but very little control. My own kids are learning piano, with a lovely teacher who insists that parents be out of the room for the lesson and who has the children take responsibility for practicing. On the other hand, Suzuki is great for developing the child’s ear. And I promise, by the second half of Book 2, the child gets more independent and it gets easier. (Unless you’re there already, in which case I’d give it another year.)

  22. Dee
    Dee says:

    Love love love your honesty. Thank you for sharing! Looking forward to reading how things turn around.
    Chin up, girl… xx

  23. Sari
    Sari says:

    “I almost cry. But I tell myself that if I'm not going to cry about [an intensely amazing relationship coming to an abrupt halt after nearly 3 years], then I’m not going to cry about [having to reschedule a surgery that I’m actually really looking forward to]. I tell myself to focus on [my Spa being named Best of State this week]: Success does not come in a linear fashion.”

    This is why I thoroughly enjoy reading. I can insert my own life into your sentences, and it fits perfectly. And when my daughter told me yesterday, ‘Mom, I just want you to be happy, no matter what,’ I cried too.

    Thank you, thank you, thank you.

  24. Heather
    Heather says:

    Great insight from the kiddo. Can’t beat those perfectly-timed, perfectly-worded moments that bring you back to a better way of thinking.

    • KateNonymous
      KateNonymous says:

      For me, at least, pretty much the same. I know my feelings about working for her would be the same if she were a man.

  25. Matt Secor
    Matt Secor says:

    I don’t know that you’re necessarily looking for advice from blog readers, but I figure that while an outside perspective may not help, it can’t hurt.

    It just sounds like getting investor funding can take a lot of time and gives uneven rewards. Is that the only way you’re gathering funds? I thought you were using consulting to fund your company. Maybe there are other options to help funding as well. I’m not very familiar with Brazen Careerist, but perhaps there is the potential for both a regular and a premium subscription, which you could charge for.

    I hope you find a way to break out of this crazy cycle of scrambling for funds.

  26. Grace
    Grace says:


    I’m all teary eyed after reading this post. Thanks so much for being so honest. Good luck to you and your company. I have a very young child with a full time job and it’s just so hard at times. I love your posts about career, parenting and dating…and I hope you are working on a next book about these subjects. I will pray that you get funding because I enjoy your posts so much. Thanks :)

  27. Dan
    Dan says:

    It sounds like this idea of a business during the Obama economy when no one is hiring is a bad idea. Just give up on it and call it a day. The writing is on the wall. I can’t imagine how someone can go on being honest with themselves with just a bunch of mind numbed followers and no one being honest with them.

    How can you be your best when no one points out what you are doing wrong?

  28. eliz
    eliz says:

    All of the commenters who are encouraging Penelope to pull the plug now have me wondering. Penelope explained to Susan why she has chosen this path, but, seriously, P, what would have to happen for you to shut down the company and say, “I gave it my best, but it wasn’t meant to be”? Is the answer to forge on forever, or as long as the VC’s come through for you? Under what circumstances would you close up shop?

    My husband is operating a business that is losing money and cannot provide him a salary. It’s a scary time for us, too, and I have had many moments like what you’ve described. We don’t know what would make us shut down, but I’m really afraid that decision won’t be ours – €“ that it will be made for us at some point. I don’t know what would be worse.

  29. Amy
    Amy says:

    Really nice post. I know the main point wasn’t about Suzuki violin, but I can’t resist saying I’m in that very same adventure/challenge right now with my daughter (age 6). Being her Suzuki practice parent has mirrored all my own faults back to me, and I swear it has given me the courage to face them like nothing else. It is one of the hardest, and most rewarding, things we’ve done together thus far. Major bonding experience!!

    Hang in there with what matters most – I’m routing for you.

  30. Laura
    Laura says:

    You are often blogging about what a bad mother you are, but you must be doing something right to have a kid with that kind of empathy. I say, don’t quit, hang in there!

  31. Tyrone
    Tyrone says:

    Once in a while, a child will say something to make you think, laugh or feel better. It’s lovely, precious and most of all true.

  32. Deadhedge
    Deadhedge says:

    My previous posts have been always been critical but this post was brilliant writing and story-telling. I’ve got a one year old and after reading this, I can only ponder what I will inflict on him.

    I would miss Brazen Careerist if it went under.

  33. Amber Warren
    Amber Warren says:

    I love reading your posts when you get personal and vulnerable. It transforms your writing style. Like you change from Penelope in pressed dark suit with reading glasses on the edge of her nose to Penelope who just stopped by say hello and vent. I love both, but the latter makes your “real” to me.

  34. deb
    deb says:

    you hit on all cylinders for me – yelling at innocent kids, being not quite organized to support them, running out of money, constantly split focus and what’s worse – an intense guilt that I haven’t been giving my kids music lessons. oy! its amazing – mother child love is unlike any other.

  35. Alan
    Alan says:

    Put up the PayPal button. needed money early on and asked for donations (I contributed). They went on to become one of the country’s leading political blogs and were widely publicized during the presidential campaign. I think they’re fully self-supporting with ads now.

  36. ka
    ka says:

    I woke today with a pit in my stomach because my daughter has her violin recital this afternoon and hasn’t practiced all week. At every violin recital no one remembers the 13th time a student nailed ‘Minute 3’. They remember the student who confused the low 2’s and high 2’s so just played middle two’s and barely made it through the piece. Right now, I am more worried that will be my daughter than I am about next Tuesday’s presentation with the VP of my company and 100 of our best customers that I’ve been prepping for all week instead of making my daughter practice. Your post made reminded me that it will all be OK.
    Thank you.

  37. Scott Woodard
    Scott Woodard says:

    “Success does not come in a linear fashion.” I love that line…

    “And he says, ‘You are trying to be your best every day, too, Mommy. You don't need to have everything be right. You should be happy for yourself.'” Out of the mouths of babes…

    Good post.

    ~ Scott

  38. Steve Errey - The Confidence Guy
    Steve Errey - The Confidence Guy says:

    That’s a smart kid you’ve got there P. You do, of course, know where he gets it from, right?

    You know things are tough, perhaps impossibly so. But you also know you’ve been here before and got through it.

    You’ll do it again, and you’ll be just fine. If we all trust you, you should too.

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