How to face cash-flow issues in a start-up


When I launched my company, Wired magazine contacted me to write a column about how to run a start-up. The editor, Dylan Tweney, blew me away with his offer. It wasn't just that he took me to lunch in the grown-local lunchroom at Wired. He also had this unbelievable faith in me that I knew what I was doing as a CEO.

Here is a confession of lameness: I said I'd write the column and then I lost confidence. I thought I didn't know enough about running a company to give other people advice.

Since then, I’ve spent two years running a start-up in the worst funding market in decades. After insane amounts of struggling, we have raised about $1 million, and for the first time, I do not feel panicked about keeping the company in business. We will have to raise more money, but I can see the path to that, and I think I can do it.

At the same time, I had a recent flurry of outside affirmation: Psychology Today featured me as a person who has outstanding resilience, and Self magazine is featuring me in their August “success” issue. So even though I squandered my opportunity to have a column in Wired, I am ready to give advice about how to run a start-up.

I'm going to answer the question people ask me most often: “What do I do when my company is out of money?”

Here is the answer:

  1. Lay people off to save money
  2. Forgo salaries to save money
  3. Make a sale to generate money
  4. Cut back your family's spending to redirect money to the company
  5. Kill your personal credit to redirect money to the company

All those options suck, of course. I should know. I did them all. And each time I wrote a blog post about how I was going nuts from funding, or making my family crazy from funding, commenters would tell me I look too crazy for anyone to fund.

But entrepreneurs wrote to me to tell me that they understand. Because most entrepreneurs have experienced something similar. They just don't write about it. And investors are not stupid: They know this is what happens to entrepreneurs. That’s why investors are investors and not entrepreneurs.

Lots of people told me to throw in the towel, but entrepreneurs never did. Because entrepreneurs knows that having a successful startup is really about not quitting. You never get the business model right on the first try. You never feel like you know what you're doing, and you always have to adjust and adjust until you find what works. If you have passion and energy and faith, you keep going.

But it has to be an insane amount of passion and energy and faith, because there is no sane reason to have a venture backed start-up. A start-up does not get funding if it is a reasonable business model. A start-up gets funded because it’s shooting for the moon, and investors fund companies to have a lottery ticket to the moon. So the odds are terrible that any entrepreneur will succeed. It is always a more sane financial decision to work at a corporate job for a paycheck.

If you can. If you can stomach it. Which reminds me about the advice my creative writing teacher gave us in graduate school: “If you can do anything else besides writing for a living, you should do it. Because writing professionally is a very hard life.” And really, making all career decisions is about knowing yourself.

So when you talk about how to manage cash flow, the crux of that question is a personal question: How much can you bear suffering in order to do a start-up? Because you're gonna run out of cash. Or worry that you are. You are not going to be able to sleep at night. You are going to start doing little, self-destructive things that add up to terribleness. Like, eat fries for sixteen meals in a row, or yell at your kids, or forget a date you made with your girlfriend.

You need to decide for yourself how much you want to do your company. It's not rational. There is no right answer. There is infinite suffering. In exchange for that, you control your own hours, work with people you love, and solve problems in areas you are passionate about.

At some point a few months ago, everyone at my company was late on rent. I had an eviction notice, two people started sleeping on sofas, and one person had no car. But none of us thought we were shutting down the company. None of us thought that was a possibility. We knew we would keep going, we just were scared about how much worse it could get.

There’s a craziness required to get through cash-flow trouble in a start-up. There is craziness that keeps people doing a start-up long enough for them to exit the start-up. A start-up is a war of attrition. Cash flow is just one battle. And right now, I feel like I’m winning. Hooray.

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    • Boot camp
      Boot camp says:

      I love to use the Fruits juices because Fruits juices are good for the health as well as for the fitness of the body. Some of the benefits are good for heart, strong bones, Growth and development of the body, sharp mind and many more.

  1. Irina I
    Irina I says:

    Penelope, I’m so happy to hear that Brazen Careerist is doing better! I hope it lasts and that you find some temporary peace :-).

  2. Stuart Foster
    Stuart Foster says:

    I tend to think that being bat shit crazy half the time and broke the other is part of the game? (Speaking about myself)

    Gotta love the confusing, multi-layered intricacies that are the VC world at this point. Wish everyone had more money though :)

  3. Jonathan Vaudreuil
    Jonathan Vaudreuil says:

    My six months immersed in a start-up was the best six months of my entire working career (so far). We had little money, I barely generated enough sales to cover my “salary” (more like monthly pittance), and everything you wrote about is so true. I had no thoughts of stopping working even though they couldn’t keep up paying me. It was too much fun. I loved it.

    I still think back to how broke and how happy I was during that period. It taught me money can’t buy happiness, it just helps you sleep better at night.

    Remember that, entrepreneurs and those thinking about it. Having money just means you can sleep better at night.

  4. Mike CJ
    Mike CJ says:

    We’ve been through all of that and more over the last seven months. Sounds like you’re on the way through it to success and so are we. You’re so right, you have to be an entrepreneur to understand it, no sane people would or could!

  5. prklypr
    prklypr says:

    Wow, this discipline thing is working! Posts 2 days in a row :) I think this post should be tied to your previous one on discipline. It takes discipline not to give in when the going gets tough, and discipline not to overdo it when things seem to be falling into place. Successful entrepeneurs are those who are willing to think outside the box, but have the discipline to stay the course when the road gets rocky.

  6. Dan
    Dan says:

    Most entrepeneuers fail. For beginners, starting your company in one of the most declining, union friendly, tax heavy northern states could have easily been “researched” as a bad idea.

    It is a relief to find out these less than stellar investors have only thrown 1.5M down the hole. For a while, I thought you were talking “real” money.

    Now I see you run a business no larger than a corner coffee shop. Good luck, you’ll need it! What companies are you going to attract as clients, per se, in “Taxconsin?”

  7. Dianna
    Dianna says:

    yes, starting or running a small business in this economy makes you crazy. I have 2 businesses and with my second business, I refuse to use my personal funds to keep it going which forces me to generate revenues. I am protecting my personal credit this time because the first time around I paid a few bills late and dinged my credit rating which is still hurting me.

    Persistence and perseverance and the willingness to put yourself last in getting paid are the signs of small business owner.

  8. Robin
    Robin says:

    Being an entrepreneur is only for the insane; I should know because I am one. I can’t tell you how many times I have cried over the state of my finances just trying to make my dream come true. So far we’ve done it all without funding but it sure would be a lot easier with it. That’s what I tell myself, anyway. After reading your trials here it seems that even with funding it isn’t easy so perhaps I should count my blessings that we’ve done as well as we have without it. Your words are inspiration for me though, as I’ve mentioned before. :) Just putting this out there helps people like me understand that you have to keep pressing on when you know you have a good idea. Change, bend, flex, whatever you have to – but hang in there!

  9. phillygrrl
    phillygrrl says:

    “If you have passion and energy and faith, you keep going.”

    One day at a time, one step at a time. I’m starting to think success comes from continuing when everyone else has stopped.

    Best of luck to you and your company.

  10. Dawaso
    Dawaso says:

    Man, does this one resonate.

    I’ve been doing start-ups for 15yrs (am 34 now), and it does take energy, enthusiasm, passion, and a bit delusion.

    Couple of the start-ups have made it and continue to grow.

    More than I can count did not. Can’t imagine doing the desk-job safe-track, though. My friends those positions love the security, and hate the security, and always seem to have an underlying dissatisfaction for not taking more of a leap.

    Anyhow, not for the faint of heart, but not a choice for some of us.

    Nice post.

  11. Eric
    Eric says:

    At last ! Congrats P’ !

    This subject speak to me very well as we (my associate and myself) have cash flow issues.

    But as we are very out of our minds, we don’t want any investor messing with our work.

    So I’m thinking about differents ways to make my company earb a bit of money in order to pay the bills. I’m thinking and building differents services aside our primary one which takes time to be launch.

    Bah. The launching of a new company in a small market where everybody knows everybody is hard. It’s working as intented. But before being really known and goes to GDC or E3 (that you know well I read), we must make a lil’ bit money first.

    We’re not looking for investor because we do not want anybody mess with our politics or who’ll telling how to do our jobs.

  12. Amy
    Amy says:

    Penelope i’m so glad that you feel like things are starting to turn a corner. Really really happy for you!

    I really enjoy your writing and read your blog religiously.

  13. Mark W.
    Mark W. says:

    When all is said and done, you will know who your friends are, who believes in you, and much more about yourself.
    Hooray. :)

  14. Happy Guy
    Happy Guy says:

    Gotta love Dan’s comment about Taxoconsin. Perhaps Penelope should’ve set up shop in those well-known tax havens Massachusetts and California.

    Because everyone knows how important tax policy is to nonunion, loss-generating tech companies.

    • Travis
      Travis says:

      Be nice to Dan. Been a very bad month for the conservative, family values crowd. Leaving angry anonymous missives to total strangers on blogs is all he has left.

  15. Steve Y.
    Steve Y. says:

    Adding to the stress is the conflict with your family life. Your significant other cannot understand why he or she, and the kids if you have them, are second place. They watch your actions, not your words, and when months of living at the office turn into years, many relationships do not survive.

    I helped a startup raise $2 million in the early 1980’s. We burned through it in a year and laid off more than half the 40-person workforce. As CFO, my mornings were spent collecting receivables and my afternoons were spent deferring payables, all the while cajoling vendors into continuing their shipments. Evenings were for budgets, accounting reports, internal memos, and meetings. After three years the company regained its footing by focusing on a specialized niche. Today it’s a well-regarded small private tech company in Alameda County.

    When we started having children, I had to make a choice. The only way my marriage could last would be to join the corporate world with its steadier hours and benefits packages.

    I didn’t make any money from those startup years, but they’ve been a source of strength for me ever since. I didn’t quit despite enormous pressure (you don’t know how you’ll perform until you’ve been through it), and I never lied to our customers, suppliers, investors, and employees despite great temptation.

    May you find great rewards and self-knowledge from your journey. Perhaps they’re the same thing.

  16. Jessica Bondj
    Jessica Bondj says:

    Hats off to all the entrepreneurs! Their struggles make job hunting look like a breeze.

  17. Diane C.
    Diane C. says:

    Wisconsin is not that bad. I grew up there, and now live in CA. (Dan may have some smart remark) Working a job to help fund my 2 businesses is not what I would like to be doing, but yes, it helps me sleep at night. Good going Penelope; it seems like forever when you’re in it, and then the next “wave” starts – you get to weed out the employees, not because of money, but getting along. Thanks for the hats off, Jessica, but job hunting to me is worse.

  18. Rick Smith
    Rick Smith says:

    Great post. I was very fortunate to build a $15m business without any funding at all (I spent $400 to buy stationary to print invoices). I have been around many struggling entrepreneurs, and know that it is very tough to get cash flow going. But there are several creative ways to get to positive cash flow quickly without raising capital or breaking your personal finances. I wrote a blog post about this, How to Start a Business with No Money (

    Be creative and persevere, but i personally would not flirt with actions that may lead to personal bankruptcy. I just don’t think you have to.

  19. Jan Hogle
    Jan Hogle says:

    “…you control your own hours, work with people you love, and solve problems in areas you are passionate about.” This is the mantra for owning your own business — and what all the direct sales party-plan companies say, too. I’m not so sure about controling your own hours… I found myself working all weekend doing parties when I would have preferred to spend the weekends with my family when the kids are not in school. I had to do calls and paperwork at night, and schedule events (parties, meetings, attend things) when other people wanted to schedule them. And yes, often you are working with people you love, but sometimes the people are not so lovable — whether you’re working for someone or for yourself. In my current job, I do enjoy most of the people I work with, and I’m passionate about what I do. I am also fortunate to have a good paycheck & benefits in this current economic mess — probably more luck than planning. What I found myself interested in 20 yrs ago now pays fairly well. That was luck. I couldn’t hack it as a small business owner (ie replace my current income) because I was unable to totally put money first. But that was a choice I made. Still, I really think your posts are right on the mark. I pass them around to everyone I know. I just feel sometimes that the independent business owner thing is not quite as wonderful as some like to advertise. It’s harder in many ways, for many people, than just having a job — especially when you like your job!

    • Anonymous
      Anonymous says:

      Depends on what you mean by “control.” I have discovered about myself that authority over my hours is critical, even if I don’t have control. I might grumble in the moment about pulling a self-imposed overnight because the work needs to happen. Having to get somebody’s permission to leave my assigned spot at a particular time feels degrading.

  20. Matt Dibble
    Matt Dibble says:

    What you say is good food for the soul of an early in their career entrepeneur. Especially the line about never feeling like you know what you’re doing.
    It’s very difficult to not question every decision you make… I can hear that little voice in the back of my head saying “they’re all going to figure out soon enough that you’re a fraud!” And I fight every day to shut that little bastard up.
    Thanks for making feel sane… for a few minutes :)

  21. Kare Anderson
    Kare Anderson says:

    This is so affirming. It’s not that I’m not acting crazy sometimes (many times?) with the start-up but that such behavior is not necessarily “crazy” to feel/ and to be… AND that I am not alone.

    Another variation of the Sofa Scenario is when several employees are sleeping on the founder’s sofa and futon and floor. Camp Co-Founder we call it.

    I remember the first time as a green reporter another journalist called a non-reporter a “civilian”. They live by different rules than us. Deadlines rule our lives – not theirs.”

    Well now in prolonged start-up role, we know first-hand that cashflow rules our work and our lives.

    Again, thank you for your straight talk.

  22. Abby Hall
    Abby Hall says:

    Congratulations on the $1,000,000!

    So now that you have some financial breathing room, are you going to create a financial plan to avoid the late rent/sleeping on the sofa scenario in the future?

    Just curious… I have no idea how far a $1M goes for you -a few months, years?

  23. Dale
    Dale says:

    this is a neat look inside the life of an entrepreneur, but what about knowing when to quit?

    How do you personally know when it’s time to quit? Is the decision pretty much made for you when you run out of money or is it when your family calls in the medics:)

    I’m being silly, but the question is a valid one especially for people who have less financial responsibilities or who are enabled by others.

  24. Mark Klocek
    Mark Klocek says:

    There is great relief in these moments of surviving to fight another day. I initially struggled with my own small start up and the fear factor before I released a game that could pay wages was immense. My gamble was worth it, I moved city to be with my girlfriend and my new child, not only am I still in love, I can also pay the rent.

  25. Danica
    Danica says:

    There are other options, too. Like with layoffs: many states have a “work sharing” program that lets companies (even startups!) who are going to lay people off cut people’s hours instead. So rather than lay off x people, they might cut back everyone’s hours – then use the work sharing program to get those employees the rest of their pay.

    Unemployment departments create programs like these because they know it’s cheaper in the long run to keep people employed through a downturn than let them be laid off and risk having to pay them full unemployment for months and possibly not get more income from them for a long time.

    Info about California’s (where I live!) is here:
    The Wisconsin unemployment department doesn’t seem to have one, but I could be wrong – and I’m sure there are others here who could use this information.

    I’m being laid off (after they cut my hours back from 30 to 10) next Tuesday, and I wish my employers had known that this program existed – I could have been making a lot more money at least while I underworked for them! It just goes to show what a huge factor ignorance can be in business.

  26. Danica
    Danica says:

    For that matter, Business Debtors Anonymous ( is a resource that every entrepreneur should know about. Their tools have helped me a huge amount in business; by following what I learned there, I set up my current business so that it can’t run me into debt. (In my case, it was inspired by stories from other people who had committed to only taking on projects that could pay for themselves in some way.)

    It’s not the only way people do things there, of course; plenty of people have more traditional businesses than I do. But their guidelines about how a healthy business is run, and info in meetings and literature about how people manage to do that, have been invaluable to me. Plus it’s free, which is nice – and very different from all the places that want to teach me a little bit about running a business in exchange for a LOT of money!

  27. Leanne
    Leanne says:

    Congrats on seeing a light/turning a corner/getting cash flow! I own and run a small business that I started in 1997 and have been through almost all sorts of cash flow highs and lows. The drama/opera of cash flow ups/downs, even though I was somewhat used to it after 7 years, almost made me want to shutdown the business in 2004 when my daughter was born. I felt like I wanted/needed more security. Then I realized that my hours flexibility would be (and are) super valuable for my family — when my kid’s daycare (and now preschool) is closed, when she is sick, and particularly if she needed to be picked up in the middle of the day, I could usually be available and my kid loves playing at my office. I keep going because I love the work, adore most of my clients, and like the flexibility to learn and evolve on my own terms. Sometimes I work long long hours day/night and sometimes short hours. To keep up my self-discipline, when work is slow, instead of just taking time off, I’ve done projects to hone my skills and clean up the office until the next paying project starts — and those self-defined projects are the ones that make me feel more confident.

  28. Alexis Martin Neely
    Alexis Martin Neely says:

    Congrats on finally feeling like you are winning, P. The other night it hit me that I’m either going to need to raise serious money for my company or sell it, but it can’t stay as it is. It’s fine, it’s a nice little money maker, but it’s never going to change the world as it is. And, if it won’t change the world, I have other, easier ways to make money. So, I’m going for it. We’re going to take things to the next level. I’m scared to death, but being scared is better than being bored.

  29. Mark W.
    Mark W. says:

    “Lots of people told me to throw in the towel, but entrepreneurs never did. Because entrepreneurs know that having a successful startup is really about not quitting. You never get the business model right on the first try. You never feel like you know what you're doing, and you always have to adjust and adjust until you find what works. If you have passion and energy and faith, you keep going.”

    Inspiration – Here’s a CBS Sunday morning show writeup and video ( ) featuring a woman who never quit until she raised enough money to have a swimming pool for kids built in her community. It took her thirty years to achieve her goal. I think you can do your startup in less time. :)

    • Mark W.
      Mark W. says:

      I just ran across this quote on the subject of quitting from Lance Armstrong which I thought was pretty good –

      “Pain is temporary. It may last a minute, or an hour, or a day, or a year, but eventually it will subside and something else will take its place. If I quit, however, it lasts forever.”

  30. Kolla
    Kolla says:

    Catching up on favorite blogs and came across this post – just what I needed to hear. In the throes of a startup, that actually seems to be working out, apart from the “have plenty of cash” part.
    Have managed to not take loans for the business but done so at the expense of melting my personal credit cards, yeah I know, not very smart.
    But, live and learn, work at it, keep the passion alive and know that I am having the time of my live doing it. Even if my diet of thin tea and dry toast is getting a little bland.

  31. Dree
    Dree says:

    Thanks, Penelope. I needed this. I’ve been trying to gather up the cojones to do cold-call marketing for my business for weeks. Maybe it’s not about cojones…maybe it’s about embracing a certain level of crazy and just being OK with it.

  32. Whitney
    Whitney says:

    Oh, this post hits me in so many spots! For my business, my cash flow problems have finally been dealt with after taking a major hit with the personal credit cards to fund growth. It was so scary to open up my credit card statements every month, and I’m so glad to be past that hump for now. No matter what type of business you are in, being an entrepreneur means working your ass off and shouldering all the responsibilities and fuck-ups that happen, and also being comfortable with the fact that you may not know exactly how all the bills will get paid… only that they WILL. I stick to it because I get to reap the rewards and benefits of the payoff, but there are times when I feel like I pay for it with my own skin and sweat. And that doesn’t always feel very good.

  33. Diana
    Diana says:

    Just a thought, interns can cut down on your expenses. They often work for nothing ( not that I really agree with this) to gain experience and you get an extra hand to help you with your work.

    • Leanne
      Leanne says:

      I agree — interns are a great way to reduce labor expenses and get some help with your work — as long as you have time to help teach the intern and not only use them for support work. I’ve seen several startups hire interns to do grunt work without ever teaching/showing the interns the ropes of what they want to learn — basically using the intern as free administrative support. I have a friend doing an internship right now where she’s being paid a stipend that’s less than minimum wage and she’s doing a combination of support/grunt work and learning about the company — that seems like the perfect internship!

  34. Melissa Chang
    Melissa Chang says:

    Thanks for writing this post. This rang so true…

    “How much can you bear suffering in order to do a start-up? Because you're gonna run out of cash. Or worry that you are. You are not going to be able to sleep at night. You are going to start doing little, self-destructive things that add up to terribleness.”

    Being in that place, it’s easy to wonder what the hell I’m doing, to think about quitting, to imagine that I’m going insane. I can’t really tell friends and family the things that I’m up against because when they ask how things are going with my company they want to hear “great.” They don’t want to know that I’ve gained 15 pounds and I haven’t taken a salary in months. But it helps me immensely to know that there are other people – other crazy, crazy people – out there who do this stuff, who aren’t going to quit, who love the fight, the chase and the struggle.

    Thanks for the inspiration. I definitely needed it today.

  35. Lance Stratton
    Lance Stratton says:


    If you are an entrepreneur and looking at starting a company, its VERY easy to put off the hard part. Which is generating sales for your company and making a profit. Believe it or not, its far easier to go out and raise enough money so you are "in the game". You can raise the money, start the company and take your chances. If you run out of money, you can raise more. Until you can't. At which point you enter the world of consulting, having learned from your experience.

    On the flip side, if you want to start and grow a business that you retain control of, put money in the bank from and can make a long term commitment to, then always remember that sales should be the first thing you focus on when you wake up in the morning. Profitable Sales to happy customers is the best path to making money. If you go to bed at night thinking about how to sell more and how to make your customers happy. You probably are in a good place. If you go to bed and wake up thinking about how to raise money to stay in business, you might as well get the new business cards and think about what your new consulting blog is going to look like

  36. Yu-kai Chou
    Yu-kai Chou says:

    Taking a midnight break from work, and saw your blogpost. I think it’s awesome that you went through another financial hurdle. We all know there will be lots more, but every jug of water is helpful for entrepreneurs to cross the desert.

    At FD, we’ve been through a lot of financial troubles and stress too, and boy is it not fun. Eventually I adjusted to the mindset that if all else fails, at worse everyone will just leave the company, and I’m by my own running the startup without salary, which is similar to the state that I started with. When I started the company, I was excited and life was extraordinary. I would be back to that state again, except that now I have a product, some users, some brand, and lots more.

    Once I think of it in those terms, I feel a bit better. However, I imagine it’s a bit tougher when you are venture backed. Being bootstrapped does have some advantages in that aspect.

    I wish Brazen Careerist the best of luck, and let me know if you ever need help with anything. Take care!

    Back to work….hope to finish today’s task by 4AM :D

  37. Zeljko
    Zeljko says:

    Maintaining a healthy cashflow is a struggle for many businesses, big or small. In fact, quite often the bigger you are the bigger you problem can be. I quite envy the ‘cash’ type of business ( coffee shop, takeaway etc ) as they don’t have to chase customer accounts. We have a Sydney printing business that struggles with late payers quite often and as a result leaves us dangerously low on funds. The main focus is of course to have sales, but to also chase your account customers and perhaps limit their account trading terms to only 7 or 14 days. When that time is up call them immediately and ask them politely for your money. Remember, the squeaky wheel will get the grease. So don’t be afraid to ask for your money. You’ve earned it.

  38. watch movie
    watch movie says:

    Unemployment departments create programs like these because they know it’s cheaper in the long run to keep people employed through a downturn than let them be laid off and risk having to pay them full unemployment for months and possibly not get more income from them for a long time.

  39. Grant Crow
    Grant Crow says:

    As I’m on my 5th start up, I totally related to this post. My most recent, is all about onine career advice for students. The US companies I’ve worked with in the past have generally taken an approach of spending big as start up (mainly on marketing) to stop competitors from gaining a foothold, but its been rare that profitability has beenr reached. I’m trying the approach of starting really small (me, myself and I) and outsourcing everything else until I really need to take staff on. So while cashflow is an issue, it’s not as painful an issue as it could be.

  40. Sami
    Sami says:

    I wouldn’t do you the disservice of assuming you are not a perfectionist:

    “Because entrepreneurs knows that having a successful startup is really about not quitting.”

    This one, I’m not sure if it’s intentional, if you meant “own” instead of “do,” or what:

    “You need to decide for yourself how much you want to do your company.”

    Your blog is the most useful thing aol news has ever indirectly introduced me to!

  41. Kieran Smith
    Kieran Smith says:

    Penelope, why is it that no matter what I type into a Google search box, your name comes up. Even as a subscriber to your blog, I’m still finding new things and running into articles that inspire me. You always have just what the doctor ordered – and for that… THANK YOU!

  42. Pariuri Online
    Pariuri Online says:

    The best answer i think is “Make a sale to generate money “, but a company must have something to sell but after that sell a manager must see that in the future the company it will look better

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