Startups are still fulfilling, even though getting funding in a recession stinks

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I can always tell when things are really falling apart for me by how many days in a row I wear the same outfit. Last week, I wore my I’m-a-successful-CEO outfit four days in a row. In case you need a visual, it is black all over with ruffle near the neck — a little bit girly and hides dirt well.

You will be interested to know that four days included one plane trip, meetings with six investors, and one date (I smelled the shirt right beforehand and it seemed okay. I didn’t think he’d be getting that close anyway.)

The last day was when I was really sure I was going to change outfits. I had an interview with Elizabeth Vargas for 20/20. I packed a huge suitcase full of everything that might look good on TV and I told myself that I’d figure out what to wear the morning of the interview. But the morning of the interview I was actually crying to my attorney about how complicated our second round of funding is becoming, and I told him that I was going to quit the company and get a job writing for a local newspaper. I really said that.

Forget the fact that local newspapers really are not hiring writers. Really. I think I was just saying it to him so he could understand how totally stressful it is raising money in this financial environment. Plus, it’s totally not cool to be admitting to such huge stress levels when you are the CEO. I mean, who wants to fund a company when the CEO is having a mental breakdown? But really, every CEO who is raising money right now is staying up all night worrying. And not telling anyone.

Well, except me. I am telling my attorney. And now you.

Okay. So I spent the morning crying and screaming at my attorney. In between phone calls with investors where I try to sound really, really pulled together. Like I don’t really need their money. Which is how you have to sound if you are ever going to get money.

And sometime during all that, I messed up time zones, and, as I was cleaning the most recent torrent of mascara down my cheek, I noticed that I was actually in the process of standing up Elizabeth Vargas.

So that was day four of my successful-CEO outfit: On 20/20. Mascara streaked. But, as I said earlier, the outfit is all black, and in a happy coincidence, so is my eye makeup.

I think the interview went well. We talked about salary and I went on my usual tirades:

All salaries should be transparent. The only people who benefit from hidden salaries are incompetent managers who are either overpaying or underpaying and don’t want to fix it.

There is no gender disparity. Women earn more money than men in their 20s and when they have kids, women choose to downscale and men don’t, so why don’t we all shut up about the pay disparity and talk about the parenting disparity?

You earn a higher salary if you are good looking. This bias runs so deep that even better looking babies get better treatment from mothers. So forget social justice and just get Botox.

Then I went back to my hotel room. And, finally, I considered changing my clothes. But before I could do that, I took a look at the community at, and I was totally taken aback by what I saw.

We are running a contest for people in their twenties to write about how blogging affected their life, and the winner gets a free trip to SXSW (a totally cool conference that I love going to each year.)

The posts people wrote are great. They provide moving descriptions of why it’s important to blog and to make sure your blog is part of a community.

So many days I think I am nuts to do this company. It’s so hard to do a startup in a any economy, let alone a bad one — the pressure to keep believing in yourself is intense, and the long hours are too. But today I am so happy to be doing a startup. Because the community at Brazen Careerist is exactly what I had hoped it would be: Meaningful conversations about things that matter to people who are earnest and honest and want to have great lives.

Here are links to eight of posts that make me feel lucky to be struggling to fund my company. Because I am lucky to be able to have my career, and my heart, linked to this community.

Nisha Chittal
“The difference between me pre-blog and me post-blog is simple: I went from an invisible, hiding lurker to a real person, and an outlier. Seems simple, but that transformation is empowering in a way you'd never expect. I went from letting others define me to defining myself.”

Milena Thomas
“It would be a bit of an understatement to say that blogging has changed my life. It’s been the most important element in leading an examined life, because of the conversations and reflections other bloggers and commenters provide.”

Andy Drish
“Mike: If you're graduating in a year, you need to be blogging right now. It'll help you get a job.
Me: Blogging? That's a fun word.”

Jarred Taylor
“On our resumes, though, we both proudly proclaimed ourselves as co-founders of the blog and included a link. And, though I haven’t independently confirmed this yet, I’m pretty sure that’s how I got my job at Google.”

Jon Bishop
“With little to no previous experience in this type of work environment, my application was in jeopardy. However, I was able to land the job on a trial bases because of my blog.”

Holly Hoffman
“For me, the power of my words is used to share what little I’ve learned, and more often than not, to show what I haven’t … blogging.. reminds me each and every day that I’m not alone, that my situation isn’t unique.”

Kathleen Argonza
“I created my blog, Tough Girl 101, to rekindle whatever spine I had before the marriage drained it away. I remembered being a tough girl once, I figured that I could be again Blogging was the first step in getting myself back on track.”

Taylor Ansley
“That’s how I’ve changed through blogging. I’m less likely to deliberate quietly on an issue and instead more likely to provoke debate. I’m quicker to throw my thoughts or beliefs into the (modest) spotlight and more likely to change my mind.”

48 replies
    • Penelope Trunk
      Penelope Trunk says:

      Not sure when the segment will air on TV. This week a 20/20 film crew is coming to the Brazen Careerist office. So it definitely won’t be online any time soon.


  1. Nisha Chittal
    Nisha Chittal says:

    Wow, so it took me about ten minutes to properly compose a response for this post. But I was telling Ryan P in an email the other day that this is really an amazing community that you guys have built, and my favorite part of this was reading all the amazing posts people wrote. I, for one, and so glad you guys are doing what you’re doing, and I feel privileged to be a part of it!

  2. Peggy
    Peggy says:

    “There is no gender disparity. Women earn more money than men in their 20s and when they have kids, women choose to downscale and men don’t, so why don’t we all shut up about the pay disparity and talk about the parenting disparity?”

    YES! YES! YES! And until women admit that they are complicit in their downscaling decisions, we cannot have a lot of other honest conversations about wage disparities, family policy, etc.

    The purpose of human existance is all about about determining what we will value and proritize, and then living out those values in a practical tangible way. Everything we value for it’s upside will – of necessity – bring a struggle with it. Our willingness to endure the struggle is how we “testify” our committment to our values.

    So, for example, the woman who says that she values being home with children over using daycare is saying that her chance to have the experience of intensive, one-on-one mothering (because it is always as much about what the mother wants as it is about what we proclaim our children “need”) is more important to her than a career and what a career provides (money, status, etc.). When the reality of this choice hits home in the form of less money in the bank, the value is tested and the mother has to ask herself again what she truly values.

    It is this continual cycle of reflection-action-refletion that shapes how we grow and develop in life. Whether it is a vicious cycle or a virtuous cycle is determined by the quality of our reflection. I.e., Is it a regular part of our life to stop and reflect on what we are doing/becoming? What resources and mental models do we draw on? Can our mental models withstand being challenged by people/ideas that are different without us immeidately cecoming defensive? If not, maybe we haven’t really thought things through like we think we have…

    Ideally, couples go through this reflection-action-reflection cycle both individually and as a couple so it strengthens their team approach to life and how they respond to the very realy challenges of providing for two critical needs in every family unit: income and nurture/caregiving. It’s a marvelous challenge when you think about it – one worthy of our best thinking and creative efforts – and certainly not one for the faint of heart!

    Hope you have a Happy Monday!
    ~ Career Encourager

  3. Mark W.
    Mark W. says:

    Quoted from above – “But really, every CEO who is raising money right now is staying up all night worrying. And not telling anyone.
    Well, except me. I am telling my attorney. And now you.”

    Maybe you should have your attorney follow you on Twitter so he can get a heads up ( “Up late ill with finance anxiety. I wish startup CEOs shared their fears instead of their chatter about how great all their products are. ”

    I think your success at funding will be much greater than finding other startup CEOs willing to share their fears.

  4. Teri
    Teri says:

    Hey, I really love your blog, but you are very wrong about the gender disparity in pay. It’s one thing to say there’s a “parenting gap” (true) but quite another to say there’s no gender wage gap (not true). Your argument ignores a whole lot of research. This is disappointing to me because otherwise I’m a huge fan of your ideas.

  5. Greg
    Greg says:

    Thanks for the suggestion to go for botox before asking for my next raise. I was thinking of showing documentation of all my recent successes and accomplishments, but now I realize there’s a more visceral approach.

    (This is, by the way, not sarcasm. I think you’re dead-on right.)

  6. Monique
    Monique says:


    I’m conflicted about Penelope’s argument that there is no gender gap. On one hand, I DO believe that many women make the choice to downsize their careers in order to care for children or aging parents. (I’m definitely a woman who fits this description!)

    At the same time, it’s also true that most male dominated industries tend to pay more than female dominated ones — and I’d argue that is in part because of the assumption that men need to be able to provide for their families, while women do not.

    My husband, for example, is a construction industry executive. Even middle management within the company gets paid rather well, and most of the men have wives who stay home. In contrast, I’m a journalist turned PR professional turned elementary teacher turned professor. Those jobs are all dominated by women — and they pay less, while requiring more education. I think that reality DOES point to a gender gap.

    Now, it’s true that women know what industries pay starting out and could make the choice to go into male-dominated industries. But the truth is, men and women DO tend to be attracted to different industries, in part because of their own natural interests and skill sets.

    Something to think about, anyway ….

  7. Dale
    Dale says:

    I think that when you bare your soul to the sun it is very hard to hide your flaws. This is what I see in blogging. People who aren’t afraid to bare their souls. I think I’ll give it a try some day when I develop the courage:)

  8. Marina
    Marina says:


    I love the sentimentality of this post! But just in case your sentimentality wears off and you start threatening to leave the company again let me try a guilt trip that might help the situation.

    I’m from a nuclear family home and I don’t have the emotional mechanisms to deal with divorce or being dumped!

    It would be like a mother bird letting her little baby stay on the cold, hard ground after she’s fallen out of the nest. Like Marc Antony leaving the Republic of Rome (do you really want Civil War to break out?) or like Madonna walking off the stage at her own concert.

    Ok I’m out of metaphors for abandonment I can summon to make you feel guilty enough to stay!

    Seriously though, I feel very lucky to be part of the Brazen community. You have no idea how much it has taught me and undoubtedly will teach me in the future.

    Hope you’re staying!


  9. Neuromarketing
    Neuromarketing says:

    Love the straight-talking commentary. One quibble – on the subject of all salaries being transparent… Unless you plan to pay everyone with a similar job an identical salary, there is a sound behavioral reason for keeping salaries private.

    Simply put, almost everyone thinks they are above average or, at least, average in job performance. Virtually nobody self-identifies as being below average, though, by definition, half of the staff will fall below a hypothetical mean.

    This means that if you have a distribution of salaries for a particular kind of position, it is likely that at least half of the people will feel underpaid and underappreciated. It’s no great loss if a few of your worst performers get the message and bail, but you don’t want to make the big middle group of steady but unspectacular performers unhappy. And even the best paid may compare their pay levels and think they deserve more.

    Best of luck with the funding!


  10. Sydney
    Sydney says:

    Alright, after Nisha’s winning submission about lurking, I’m un-lurking.

    Though I don’t know what it’s like to get funding for a startup, go through a divorce or parent children, I do know a bit about mascara and it’s removal after a torrential downpour from your tear ducts.

    Neutrogena oil-free make-up remover. Pale blue bottle. One swipe and you’re free of the smeared bat shit all over your put-together and totally-prepared-for-this-meeting face. (I was once told that mascara is made of bat shit, yet to confirm)

  11. jrandom42
    jrandom42 says:

    Another shallow post by the princess of shallowness. What I’m hearing her say, is that for those of us who weren’t born beautiful, and who can’t be made beautiful by surgery or any other means, you’re screwed. And not only are you screwed, you’ll continue to be screwed the rest of your life, because people only care how good you look, not how smart, skilled, competent and accomplished you are.

    I still think Judge Judy had it right: “Beauty fades, dumb is forever.”

    Roger, sounds like you’re talking about the Lake Woebegon Effect: “where all the women are strong, all the men are good-looking, and all the children are above average.”

  12. Missa
    Missa says:

    Penelope, I admire you for being able to wear the same outfit 4 days in a row! I wish I could do this. I’m primarily a “wear it once, throw it in the laundry pile, run out of shirts because I haven’t done laundry, buy a new cute cheap shirt” and continue the trend because my friends/co-workers seem hardwired to compliment me on my appearance when I’m wearing something new.

    Gosh, I once donated a really cute dress because I wore it on vacation and had “too many pictures of me in it” to ever wear it again. I thought people would think I only had one dress. I realize this is nuts…

    I’m now trying to edit my wardrobe and find timeless pieces that fit properly and make me look fabulous no matter how often I wear them. I’ll just always give them the smell test ;)

  13. Ashtacular
    Ashtacular says:

    Personally, I would rather have a CEO who cries and stresses out…then a stoic one who hoards all of their endearing human feelings. The down to earth higher ups throughout my life have been such deeper inspirations than the impenetrable dickhead types. Those kinds of leaders have their place in teaching the peons how to rise above, as well as skillfully dodge and bulldoze pricks,… but the stripped down, genuine kind of leader who lets their people in a little bit, is the kind who truly becomes a mentor, thus turning the peons into badasses. BTW, as you know- SXSW…the greatest conference on earth, takes place in (my home) Austin, TX…. and I don’t know if you plan to speak when you come to the conference, but if you do….I must attend and bring my other kick ass entrepreneurial bitches who would “get” you. Do keep us abreast…..

  14. Jennifer
    Jennifer says:

    I find it interesting that, from the quotes you pulled, the female bloggers were focused on introspection, self-fulfillment, and personal growth, while the male bloggers were focused on using their blog as a way to get a job that they wanted. Could this also point to a reason for gender wage disparity?

    Also, about the parenting thing — I am 36 y.o., no kids, been in the professional world since graduating with a BS, since earned an MBA, yet I have always earned less than my less educated, younger, male counterparts. I think the wage gap has more to do with the fact that women don’t ask for what they want or deserve, where men have an easier time with self-promotion.

  15. avant garde designer
    avant garde designer says:

    The clothing discussions make me smile. I quit my day job several years ago and now work out of my home. Additionally, I’m from the Midwest (note Penelope’s recent discussion on our lovely fashions). I can go days, even all week, wearing the same black yoga pants and scruffy t-shirt. At some point, I realize I should probably shower before my husband comes home.

    Amazingly, I’m still quite productive! In fact, it’s very liberating knowing I don’t have to play the stupid fashion game just to get ahead. That is, until I have to meet with a client and realize I have absolutely nothing to wear.

  16. Raven
    Raven says:

    BC is a wonderful community – I’m glad I discovered it when I did. I especially agree with the salary issue as someone who has had to deal with the hostility that comes from co-workers and managers when I wanted to be more open about salary transparency.

  17. NewEngland
    NewEngland says:


    I am thinking of going your career route. I am also a journalist turned PR executive with teaching credentials. Have you written online about your experience switching from the media world to teaching and then to academia? I am really interested in speaking with people who have done this type of career switch.

  18. Paul
    Paul says:

    I wasn’t quite sure if this blog went from raising money in a bad economy to blogging and it’s effects on people, but the title subject is what brought me in. Having worked on various start-ups and now engaged in yet another, I’ve found it’s not too difficult to raise some kind of money. I mean if you really believe in an idea, you should be able to convey that belief to someone else, hopefully someone with money. The problem is that with that venture capital, you have to find some middle ground on control. Personally, I like to be in control, so avoiding venture capital while keeping a growing trend is a goal for me!

  19. Jessica Bond
    Jessica Bond says:

    Attorneys are typically paid by the hour so the more time one spends using them like a therapist you are decreasing your net worth (i.e. in a divorce) and/or available funding for your business (i.e. in a start up).
    Therapists rates are typically lower than the attorney hourly fee.

  20. Yu Ming Lui
    Yu Ming Lui says:

    My boyfriend was one of the top execs involved in raising funds for the start-up he worked for and it’s hard, even in good times. Penelope, just hold on, because you never know who’s around the next corner who will believe in your product and company.

    Nisha Chittal’s quote puts into words about my own personal development with my blog(s). Brazen is an amazing community.

    Re Maybelline eye makeup remover – that stuff is good, and cheap. Thumbs up for that solution. I would recommend Shu Uemura’s Cleansing Oil but they don’t ’em in travel size.

  21. Marsha Keeffer
    Marsha Keeffer says:

    One of the biggest differences between you and other CEOs – you’re transparent. Good to hear the trials and tribulations of the funding process discussed with such openness. I love the way you continue to show such incredible tenacity, even while feeling like dropping the whole thing.

  22. Mary
    Mary says:

    Check out . To me, most of the women appear average — to maybe even slightly below average in looks. Maybe talent and ambition can trump attractiveness. My advice would be to spend a lot less time worrying about your looks, (as long as you’re not overweight — that’s an energy and health issues as well — so you need to do something about it) and more time on honing the qualities that make you unique and valuable to your business.

  23. Rubi
    Rubi says:

    Yes, I was thinking what are women who don’t look conventionally attractive supposed to do? What about their genes giving them a certain look? Should they go through drastic measures beyond Botox? I think not.

    I think that, given that you see many people married of all attractiveness levels, it just goes to show that we are not all attracted to the same type. It might end up the same where you work. Your last boss or your last group of coworkers might have found you attractive but at your new place there’s either a new alpha female or you are just not their cup of tea.

    How do you make a start up attractive? Put lipstick on it or what?

  24. Leanne
    Leanne says:

    As usual I love your candor. Working from home I’m often in the same outfit for many days – but it’s usually sweats.

    Thank you also for speaking up about the pay disparity. I blog on and I received a comment about how unfair it is that moms who take time off from their careers can’t jump right back in to the executive suite – she felt it was sexist. I felt it was not. I think if a man takes time off to raise his kids (which is rare but happens) he, too would not be able to jump right back in to his VP slot – we may never know because of the parenting disparity, though.

  25. noone
    noone says:

    “And one date” Penelope. You sure don’t waste any time do you? Has it even been a month since the Farmer?

    I’m thinking you need some alone time. Too much spilling your guts online and going from one man to the next is not a good sign.

  26. gregcnora.aim
    gregcnora.aim says:

    Backing Penelope’s point, I live in a big city Metro, and aside from small business owners who are self employed; I cannot think of a single ugly or really short person that is paid really well. Nature is cruel I suppose.

    • Mary
      Mary says:

      I live in NYC. I know someone who is paid very well, and is both ugly and short. And she’s a woman in a male-dominated company.

      So, what exactly does this prove? That nature is not cruel? Talk about circumstantial data.

  27. Alora
    Alora says:

    While I completely agree that the mommy-track has a significant impact on the career progression (and therefore income disparity) between men and women, I disagree that is the ONLY cause for pay disparity between the genders. Female dominated industries (nursing, call centers, office administrators, etc.) all pay less, on the average, than their male-dominated counterparts (most trades, sales, etc.). Yes, there is a parenting disparity (hell, there is a large-scale DOMESTIC disparity: even among childfree couples the vast majority of housework falls to the female, even if/when she is the primary breadwinner), but to say that is all of it strikes me as a bit disingenuous and simplistic.

  28. Monique
    Monique says:

    Nicely put, Alora! You made that point much better than I attempted to a few posts back.
    I have switched careers a few times, trying to find at least some semblance of work-home balance, while also trying to make an income that is not borderline embarrassing. The skills more commonly found in women simply aren’t valued, because there is sitll a sense that the pay of women is an “extra” at home. It IS a problem. Thanks for the post.

  29. Marianne
    Marianne says:

    Hi – I’m new here, visiting via today.

    I’m cracking up at your description of wearing your CEO outfit four days straight since I freguently wear my CM[om}O jeans all week long.

    I’ll be back – I can’t believe I haven’t stumbled across you before today. I need to take off my bloggy blinders.

    Nice to meet you.

  30. Promise Phelon
    Promise Phelon says:

    Penelope, I literally laughed out loud when I read your post. [I too have yelled at the attorney.] These are trying times for startup-CEO’s trying to raise money. There are days when it goes from maddening and saddening to absolutely comical. We’re all struggling to fund our companies, but I keep telling myself “the strong will survive.” I have my “wire me the funds” suit that I’ve thought about wearing 24-hours a day in case I run into an investor while sleep-walking or getting the 6AM coffee from Starbucks. The process of raising money, running a start-up in the worst of times and knocking on five times as many doors has caused me to search deep… I don’t know about you, but I’m more committed now to my company–more than I would be if it were easy to get there. Keep it up–you have a vision for something bigger than you! It will happen and will be bigger and better than you expected. If you’re ever in San Francisco, I make a mean Sidecar. Good luck, Promise

  31. kerrjac
    kerrjac says:

    Completely off-topic but I was reminded of some of your thoughts Penelope while reading Zen & the Art Motorcycle Maintenance this week. It’s the second time I’m reading it (1st time this decade), but really the authors thoughts made me more productive this week: The idea of seeing your work as a craft, a logical extension of you, rather as something separate; the importance of quality; taking your time; and fully immersing yourself. For instance, I suddenly realized how silly it was that I’d been listening to music half the week. It’s not that the mundane parts of my job are boring, it’s that I wasn’t approaching it in the correct manner. Doing the same projects I was much more engaged, it just felt good. Anyway, I’d be curious about your thoughts on the book, or recommend it if you haven’t read it, as it goes much deeper than the pieces above. In time it’s just become more relevant.

  32. Mark W.
    Mark W. says:

    I would guess this quote would describe the fulfilling part of your startup –

    “When you are inspired by some great purpose, some extraordinary project, all your thoughts break their bounds:Your mind transcends limitations, your consciousness expands in every direction, and you find yourself in a new, great, and wonderful world.
    Dormant forces, faculties, and talents become alive, and you discover yourself to be a greater person by far than you ever dreamed yourself to be.”

    Patanjali (second century B.C.)


  33. kerrjac
    kerrjac says:

    Yeah Mark W. I think your quote puts it perfectly. The only thing I’d add is that too often people are just not inspired, and then they see this as a reflection of the world rather than of themselves. When you turn it around like this – realizing that the apathy is from you and not the world – suddenly there’s a lot to be excited and engaged about. But it’s not just a silly little mind-trick. It’s accepting the world for what it is but refusing to accept the status quo, innovation.

  34. Curmudgeon
    Curmudgeon says:

    I have the opportunity to talk to tech industry CEOs all the time, and you’re right about the funding, seemingly due to the credit freeze. One had his funding pulled and had to close the company, while another had just closed his second round, and was told he had to become profitable on that.

    I’ve been thinking about Botox. But I’m a man, and have just started reaching the stage where the sagging facial skin makes me look rugged and distinguished. I think it will have to do for a while.

  35. Jonha
    Jonha says:

    It’s been a while since I last visited your blog and I just love your old posts. Not that I don’t like the newer ones especially those with pictures, but the older posts reflect the times when you tried to make a difference and it inspires me that you are NOW enjoying the results of all those sacrifices. I thought about how I could reach out to my posterity and the single most effective, efficient and probably the cheapest is Blogging. And that’s one change that would not only affect me but also to the generations that will come. I dream about the day when my kids and grandkids will sit in front of the computer and read about my thoughts on things, consult me like I always consult you about various things and take my advice even if I’m no longer with them.

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