Getting Back Your Series A Mojo

Posted on Jul 27, 2013 | 43 comments

Getting Back Your Series A Mojo

Last year I wrote a blog post on entrepreneurs with a chip on their shoulders.

I think it’s an important read. A chip on one’s shoulder as in, “Fuck the system, it’s broken and I want to fix it” is exactly the energy I look for in entrepreneurs.

My internal compass says that “country-club” entrepreneurs struggle to make as big of an impact because it’s really hard to totally change a system that you’re part of and have a vested interest in. It’s hard to be a rebel when upsetting the apple cart affects a bunch of people like you.

Take Maker Studios. What I loved about the founding team from day 1 was that the founders were all people who tried to break into Hollywood and found the system closed. So their view was, “fuck the system, let’s create a new one on YouTube.”

On the other hand, if the chip on your shoulder is, “I’m not treated fairly by the system, boo hoo, I’m different and that’s why you aren’t helping me” that chip can be a big negative.

I see this a lot in funding where an entrepreneur has struggled to raise money and spends all their time lamenting how lame investors are.

My friend Seth Levine covered this well in his blog post on “Handling Rejection” which you should also read. (and if you haven’t seen 20 Feet From Stardom, which this founder talks about in his letter to Seth, you must. It’s this year’s Searching for Sugar Man. I loved, loved, loved 20 Feet).

Seth responded to an entrepreneur’s request for financing and the entrepreneur wrote back a nastygram. Nothing good ever comes from that – even if you are right.  Seth is one of the most decent human beings in the venture industry so the rant was off base. But even if a VC is nasty a rant email back isn’t the right way to channel your frustration.

The best revenge for rejection is success. The best lesson learned for yourself is self reflection. “If my objective is raising capital and I’m struggling, what can I learn about those who do get funded and how can I improve my odds by changing?”


They often come from the experience of being kicked, rejected, shunned, beat up. Then the victim looks around and sees everybody else is having it so easy even though I’m better than they are. So it’s “poor me, the system is fucked.”

But there is another more prevalent emotional swing than the hero to chip angst. And that is the “loss of confidence” vibe. It’s the puppy-who-was-kicked-and-now-walks-around-with-his-head-down syndrome.

And it’s everywhere. I could link to a bunch of blog posts that come across this way but prefer not to single anybody out.

Here’s the deal.

When you started you had the youthful (from a company perspective not age) energy, enthusiasm and naïveté that comes from actually thinking you can change the world. Nobody goes into a startup expecting to fail – we all imagine the next big startup movie is going to be about us. Our inner script is heroic and the struggles are mere battle scars on the inevitable journey to slay King Joffrey.

But reality sets in after the first few battles. You raised your seed funds. You got your tech press and your parents are proud. You old high school friends suddenly reached out on Facebook. You build a team, ship your product, more tech press, more funding.

You get invited to speak on panels. You attend speaker dinners. You have dinner outside at a quarter mile dinner table. You’re on top of the world.

Except that building a successful startup is hard. And back home when you land and come into the office on Monday your staff still knows the truth. Your app isn’t getting enough repeat visitors. Your churn rates are too high. You have an eCommerce company and have to much unsold inventory. Your lead developer quit to join the new hot thing.

It happens to nearly every startup. Nearly every one. I had lunch last week with the CEO of a publicly traded tech company. We shared stories about our past rejections, about our inability to raise money in down markets, about the weeks left in cash, about how we were sure we were dead. We found a way through it. He did even more so than I did.

I had a similar chat with Matt Coffin of LowerMyBills (blog post & video here) where he tells his similar story. Nearly bankrupt. Begging for money. And a few years forward and he sold his company for 100’s of millions of dollars.

My point ….

We’ve all been there – every entrepreneur. You start off by believing your own hype, drinking your own Kool Aid.

And then you meet reality.

And some entrepreneurs can maintain their enthusiasm, optimism and energy: Working hard and staying positive.

But that’s hard.

Many still put in the hours but you can see the stress in their eyes and hear it in their voices. In stead of telling people how they are going to change the world they start to show self doubt. They qualify every initiative with, “well this didn’t prove viral adoption last time so I don’t expect a silver bullet this time.”

Sometimes the silver bullet does come. Often it doesn’t. Usually success is about working hard enough and long enough and eventually getting a lucky break. Another meeting last week with a different founder who sold for 100’s of millions and is not an active angel, “Startups are hard. I don’t know if I should keep investing in them. So many are struggling I feel like all I’m dealing with are problems. I wish more young people understood what a role luck plays into a huge success.”

And of course – the harder you work, the luckier you get.

But in order to make the magic work another few months, years, you need to keep up blind belief in yourself. Confidence is THE single most important attribute in being able to attract money, hire staff, stave off creditors, get press, do biz dev deals, close big sales and one day sell your company.


That magic you had at your Series A.


You need to dig deep.

As a friend who is running a startup focused on “the mind” said to me (my words), “why is it that it is accepted wisdom that atheletes need to visualize and focus on positive energy and confidence and when we say this to business people they think it is self-help, airy fairy stuff?”

He’s right.

Mental toughness matters. A lot. Confidence matters more.

I personally am not prone to depression or substances but I know many who are. Depression isn’t talked about openly enough in our industry. Nor is general mental well being.

I wish more startups would get personal coaches so they could let out their angst to neutral people – not staff, not investors. It’s why YPO is such an important organization.


If you’re in a startup that has struggled know that you’re not alone – we’re all naked in the mirror in the morning.

If you’re in really bad shape (10% of you) – seek help. Life is more important than your startup and there is always another day. Your reputation won’t suffer if your business does. You can evolve.

If you’re in the norm (85% of you) please think about how to let out your steam, talk to others, get mentors, re-find the energy / confidence, or bring in new staff who can help re-energize you and/or your business.

If you plan to raise more money, improve your business ops, or sell your company you need your Series A mojo back. You need to rekindle that feeling, rediscover that belief in you and your company’s mission.

If you’re crushing it (5% of your) mazel tov.

And finally …

Since I have this conversation private all the time …

No. I’m not talking about you.

post script: I wrote this in one sitting before racing out the door on a long-weekend vacation with the family. No edits / no spell check. Apologies for any rambling, incoherence or typos. I may try to come back and edit later but want to get back to the family!

  • jonathanjaeger

    “Why is it that it is accepted wisdom that atheletes need to visualize and focus on positive energy and confidence and when we say this to business people they think it is self-help, airy fairy stuff?”

    Hmmm, not sure if most business people shun the “positive energy” self-help type stuff. A lot of the business books that are popular are really just self-help books with a hint of business (think Crush It, Just Listen, 4 Hour Work Week, 7 Habits of Highly Effective People, etc.).

    Personally I like the study that says that fake smiling improves your mood and outlook. If you’re not happy, force yourself to smile and eventually it will be a self-fulfilling prophecy and you’ll feel better. Sometimes you need to get out of your funk by forcing yourself out of a funk.

  • Alex Cook

    Spot on post Mark – thanks.

  • Alex Quilici

    Great post. Lack of confidence is a slow-motion death spiral. And it’s really hard to fake after you’ve been beat up. So the really key thing to remember is that nothing brings back true confidence like results, so the main way to get confidence back after getting beat up by investors or rocked by bus dev that falls apart, is to focus on and figure out how to make your business work without them. That’s tough, and will take time, so one key is to define a path of relatively small but meaningful steps to hit and focus on (reduce churn by 10%, improve reviews from 4* to 5*, increase paying conversion, get a smaller partner going, etc..). It often doesn’t take too many of those to put a company in a completely different position. And as part of that, you need to work really hard to getting even part-time new blood to the team tin support of those results. It’s baby steps but before long you’re across the room, and your confidence starts coming back.

  • David Tuck

    Hi Mark. Thank you for this and all your other posts. I find them invaluable as a fledgling entrepreneur.

    In talking about country club entrepreneurs, you say that “It’s hard to be a rebel when upsetting the apple cart affects a bunch of people like you”.

    I qualified as an accountant with a big 4 firm, but am now a finance SaaS entrepreneur. My, granted somewhat vested, viewpoint is that being one of those people makes you infinitely better placed to identify how the apple cart can be upset in the first place.

  • Rachel Aubrey Morris

    Such an important topic because we’ve all experienced low confidence at some point and it’s effects are disastrous no matter your job level. Having an entrepreneur for a Dad, he taught me early on to stop thinking of confidence as a result of what’s happening externally and to cultivate confidence as a habit. Something you can lose (get out of the habit) but just as easily something you have the power to build back. Part of leading is cultivating this habit in the people around you – which surprisingly is a great way to rebuild it within yourself. Great post, Mark.

  • Dale Larson

    Many of us were attracted to technology because it can be understood in rational terms, yet winning at a technology startup is at least as emotional and relational as it is technical and rational. We have to grow ourselves at the same time we grow our companies, or we hold ourselves back and get in our own way.

    Confidence is fascinating because it has so many aspects. One starting point is normalizing a lack of confidence, and letting yourself experience it fully (at least some of the time) when it does come up. Know that even the most successful entrepreneurs sometimes fear that they aren’t good enough, and everyone else will figure that out soon enough. It’s a lot easier to work with from there than when you think “nobody else feels like that, it’s just me.”

    There are lots of great tricks and shortcuts to boosting your confidence, resetting your state, or appearing more confident than you are. All can be useful to entrepreneurs at times. But making the long term investment in yourself (and by extension,in your company), of doing the broader work of growing as a person and as a leader in other areas leads to many more benefits, and a deeper confidence comes along naturally. That’s why good coaches are so beneficial to entrepreneurs.

    To the extent that it’s true that “Confidence is THE single most important attribute in being able to attract money, hire staff, stave off creditors, get press, do biz dev deals, close big sales and one day sell your company,” then confidence is a good signal for a lot more awesome things going on along with it. In fact, we’ve probably all been taken in occasionally by someone who projected a kind of confidence. Then we learn later that they were a great salesperson who couldn’t really back it up — they weren’t living it. But when you are showing up as someone who cares deeply about the people you work with as well as the product you build, are self-aware and have interpersonal intelligence, when you are decisive and collaborative, have composure, productivity, and passion and are purposeful and visionary; from that place you have a kind of cool, humble confidence that’s incredibly appealing and enrolling.

    Thanks, Mark. Your posts are always interesting and often provocative, and I’m glad you added your voice again to the discussion about the inner work of entrepreneurs.

  • marklanday

    Nice post. A paid ceo coach is helpful to work through these ups and downs. Not just a board member. The investor community need to become more supportive of having this as a budget item from the get go, and not waiting until there is a crisis.

    Mark Landay
    Dynamic Synergy Executive Recruitment

  • RogerVaughn

    I liken startup life to building Rome. There were several battles wherein victory was all but assured, – the startup was under-funded, under-staffed and likely to be crushed but found a way to grow primarily through creativity, better planning, and some “luck”. Losing a single battle doesn’t mean the entire war (for the minds and wallets of customers) is lost, though certain battles are of course pivotal. Mad props – love the posts Mark & I read every one.

  • Andy Wilson

    I think the challenge we entrepreneurs face is that we start with grand ideas . . . . otherwise why bother (heck. . . we want to change the world). But rarely is the grand idea achieved in a single bold stroke (Instagram outcomes are truly 1 in a million). So while we must envision getting to the top of the mountain and planting the flat on the summit (the big vision), we most primarily focus our team and energy and resources on getting to the next base camp (which often is still no mean feat). So by breaking down “the climb” into key achievable milestones, you get the sense of meaningful progress toward the goal while avoiding the disappointment of not making the summit in a single stroke. By taking this perspective, I have been able to keep myself and my start-up teams “in the game.”

  • Siobhan Bulfin

    brilliant piece. I’m ever grateful that I’m a Pollyanna and am focused but I know at times I’ve been guilty of blaming the system and self-doubt.

  • Miisa Mink

    Thank you Mark, your posts are always insightful, honest and helpful. Lots to learn, and I totally believe in the endurance of confidence. The way I see it (my entrepreneurial journey), I’m a human test lab on how to get there. There is no such thing as failure, just different combinations and permutations of work and daily habits that will eventually bring results.

  • Eric Friedman

    Confidence is also contagious when it comes to your team. Attitudes are what are really contagious and whatever you are exuding, they will pick up on it. Not just for outside partners, potential clients, or investors – the people you spend the most time with. Its important to keep a positive mentality around the people that are actually building the machine as they will mirror your mentality. Its ok to get down sometimes and have a cofounder cheer you back up, but its not ok to be down and out and negative all the time.

  • Parham Beheshti

    Great piece.
    But I think luck doesn’t play a major role in general success.
    A bad idea can’t get lucky and turn into something big, great ideas along with dedication will eventually find their way through tough times, some great ideas may get lucky and make it huge.

  • Jess Bachman

    Where does blind belief and confidence end and delusional “we’re crushin it!” rhetoric begin? Is there room for honesty? If so.. which whom… when?

  • Roham

    spot on post as usual, Mark. i think this is one of the key benefits of hanging out with other (non-competitive) CEOs. sharing war stories helps keep things in perspective.

    jason’s talk with jerry colonna comes at this from a similar angle:

    that said, always a difference between confident and delusional, and a smart team can spot bluster miles away. i’ve found that being honest about the fact that problems exist helps build trust; and the ensuing war speech to build confidence is that much more respected and appreciated because it’s coming from a position of transparency.

    this TED talk about vulnerability is also an interesting look at things:

  • I Gotta Go My Name Is Joe

    Oh Mah Gawd I needed to read this… Mark.. you’re the freaking best with the “getting kicked in the ass, run over, and left for dead” stories of woe. I mean that seriously… hardly anybody talks about this stuff, and you keep going and going and going and I’m so grateful to you for that… for those of us that can’t get off the couch for months after an ultimate ass whipping, we need to know we’re not alone… because God Almighty it’s painful.

    I’ve almost got my mojo back after getting kicked in the face in addition to having all my teeth knocked out (figuratively of course) oh and suffering PTSD…. it was a bad one…. worst kick in the face I’ve gotten in my professional life that’s for sure….

    Even though the launch of my project was publicly a huge success… the dark underbelly was something ugly. I was working with literally some of the most high profile if not one of the top five people on the planet who will remain nameless, but bigger than anyone in the Valley and we’ll leave it at that…. ( i bring this up not to drop, but to preface how this of course attracts the crazies)

    What happened next? I got the ultimate hoodwink….Some of these greedy mutha funkers saw who was involved and did some shady stuff banking on the fact they were somehow going to bank… these folks did some crazy scapegoating, tried to frame me for criminal shit to the point where I will likely and unfortunately sue and win beyond one’s wildest dreams… and I don’t do litigation, cuz we all know what that looks like and it’s a waste of time unless it’s not and in this case it’s not.

    After having a successful launchlllllthe jealousy and evil shit kicked in and people wanted to kill me, threaten me… you name it….they wanted to threaten me and defame me into owning my product/brand….. I really had to question things… like “do I really want this kind of life because this is nuts and is it worth it?”

    So… I gots two questions for you Muster Suster… :) (gots isn’t grammatically correct FYI. yes I know… but it sounds more fun or something just right at this moment)

    1. I’ve been MIA for the past few months, my mojo was killed and buried although I just saw it last week and it was still rising from the dead…. so the good news is it looks like it’s on its way back…

    I’m such a perfectionist…. and the fact that serious misinformation is floating around to a few folks… really bugs the living shit out of me…. I don’t know what they think… although my friends in AA, I’m not in AA, tell me “what other people think of me is none of my business.” So with that…. how do I move forward without being paranoid people are thinking bad shit about me? Or is the answer.. just don’t care..? Cuz that’s a tall order because who the F doesn’t care? Please help cuz you’re really smart about this n stuff.

    2. I have serious confidence issues with getting completely f+cked over again… like really bad…. NOW… how do I get past this? I’ve got amazing opportunities and I keep delaying because I’m scared to death or ask myself do I have it in me again to go and raise $20M USD right now and even if I do.. do I want to raise $20M because I know how crazy people get when the money hits….things get wacka doodle doo and people do weird shit (the bad people are obviously gone, seeking new tribe, already had a tribe on the periphery that kicks ass)

    Ok give it to me… the smackdown…

    your friend in business f’in chaos,

    p.s. the shit these people did to me was seriously evil.. how evil have you seen it get.. it might make me feel better cuz your stories always make me feel better and not like such a leper.

  • Scott Barnett

    Luck by itself doesn’t usually play a major role. But hard work in combination with luck is usually the winning formula. Hard work without a little luck usually results in a single or double instead of a home run (at best).

  • Scott Barnett

    I liked the flow of this post, so if you want to keep writing when you’re racing out the door for a long weekend, I won’t complain :-)

    This is great stuff, I’m almost done with my own post on handling stress at a startup and I’m going to reference this. Something I’ve been working on myself is the seeming dichotomy of being really upbeat/excited about your idea, but also being realistic about the roadblocks ahead of you. No matter how good things look right now, you’re going to be in the trough of disillusionment at some point in the future – guaranteed. If you can reconcile and manage these conflicting emotions (and help your team to do the same) it gives you a serious leg up.

  • Gene Massey

    Thank you Mark for all you do for us. Terrific and extremely valuable post for all of us.

  • petermengo

    This week – for the first time in years – I got sick. A mystery virus I picked up while spending time with a family member in the hospital (stay out of hospitals!). I had forgotten about the mental beating your self-confidence takes when you’re sick. Suddenly my startup world went from tough but conquerable to “we’re freeqin’ dead”. I went into super procrastination/paranoia mode.

    Fortunately a friend talked it out with me and as the virus passed so did the mind-set. Between that event and you’re killer, timely post I cemented what I inherently knew was true but had ignored – STAY WELL. I’m going to double my focus on taking 30 mins a day to exercise and think (at the same time). Nothing seems to re-gen my confidence like those two things … or closing a sale/round.

    Book plug –> If you think it’s tough – read or listen to this.

    “Unbroken” by Laura Hillenbrand (author of “Seabiscuit”).

    No doubt one of the greatest stories of human endurance EVER. Puts life into perspective.

  • Elia Freedman

    I’ve been doing running a company for a long-time now. There have been some very good times (involved with iPad launch) and some very bad times (had to lay off 80% of my team). But I keep going. Sometimes I will be asked why I persist. And I always say because opportunity is for those who show up and for those who are looking for it.

  • Cookie Marenco

    Great post Mark. Confidence is a huge subject. Confidence is accepting your decisions regardless of outcome while learning from your successes and failures.

    Founding a startup is a little like being Christopher Columbus. You’ve got to convince a lot of people that “India is a short boat trip from Spain”. You raise the money from Queen, convince the ragged crew of riches, then somewhere along the line, the crew wants to mutiny cuz it’s taking longer than you thought and scurvy is setting in. :) Columbus was a failure at finding India and instead found a whole new continent. Columbus had a lot of balls to pull that whole thing off.

    Being an entrepreneur is about belief, adventure and discovery. You’ve got to thrive in risk and chaos to welcome the rewards — which aren’t always financial. You’ve got to be able to pick yourself up after being beaten down.. You learn to say ‘no’ with respect and say “yes” while everyone else is saying “no”. There is no time for regrets and complaints.

    But luck… I don’t really believe in “luck”. My definition of “luck” is having the tenacity to put yourself into opportunistic situations. That’s keeping your doors open long enough for luck to walk in and hope you recognize it. Right place, right time is over rated.

    Some good news… Next month, NPR/All Thing Considered is doing a featured piece on me, my business and the ground breaking work we do with new digital audio, DSD. And our relationship with a major consumer electronics company is about to give us incredible exposure. We worked hard for this ‘luck’ to happen. :)

    Mark, I do want to thank you for your ‘arms length’ mentoring. Through the ups and downs, your posts have helped me stay on track and are a reminder that I’m not alone in with a vision. Your advise is always timely!

  • TJ Culbertson

    Agreed. This is a great post that needs to be on the calendar to reread every 3 months to stay on course – thanks for writing.

    At the very early stages, nobody operates with full confidence – at least they shouldn’t IMO. It ebbs and flows, which is natural. I think it helps to have a core purpose that is bigger than just “running a company” to rely on for support when doubt creeps in. And then just keep fighting – stay alive one more day because it only takes one investor/customer/partner to buy into your vision.

  • Modify Watches

    Thanks Mark. We’re in the 85%. Grinding every day, and enjoying it. But appreciate even the small boost during those times when it feels like the 10%.

    When those happen, and articles like this don’t appear, what’s been your strategy to stay positive and fight the good fight?

  • Dale Larson

    Right, a coach is a completely different conversation than with a board member or others. For many CEOs, their conversations with us feel like the only place they can safely/completely open up to about the ups and downs. (Because our work is confidential, because we don’t have any agenda other than to support them, and because of tools we bring and the way we approach our conversations.)

    As far as investor support, we haven’t run into investor objections to coaching budgets for founders, even though most of our clients come through referrals from other founders (rather than from boards). Some come at a time of crisis, but more show up presenting #firstworldproblems like overwhelm and trying to scaling their own growth to keep pace with success and rapid growth.

  •!/gentschev Greg Gentschev

    I used to think time was the most limited resource, but now I believe it’s actually all those squishy mental qualities – self confidence, willpower, focus, positivity, etc. Being able to regenerate those faster than the average person in the face of hard knocks is perhaps the single most important quality for being successful at doing anything truly difficult, like a startup.

  • Lisa O’rrell

    What a great lesson & teacher – there is so much wisdom in psyching yourself up continually. It may take YEARS to get ‘results’ when you are pursuing the Giants in a global industry. It’s been a constant struggle to not lose the original vision & stay the course WHILE pivoting the idea temporarily to get a foot into the market. Thanks Mark & Rachel!

  • marklanday

    Nice to hear from you. Long time.


  • Kirsten Lambertsen

    You’re a good human for posting this :-)

    I’m in the struggle right now, and it’s taking a new level of positive thinking and zen attitude to keep from losing it. But I’m learning some pretty great things at the same time. I’m daily how much doing a startup is like being an artist… oftentimes the best work comes from the greatest struggle.

    I encourage startupeers to join and really get involved in a co-working space. This is where your tribe hangs out, where you can commiserate, get encouragement, get moral support, and be reminded that you’re not the only one. My two startupeer tribes have been crucial for me. And I like being of a use to them, too.

    Now, I can report that we have found a light this last week, something really truly great that we wouldn’t have discovered if we hadn’t gone through the lean times up to now. So, ya’ll, if you’re in the struggle, hang in there!

  • Darren Marble

    Mark, this is one of my favorite posts of yours in a long while – thank you for inspiring me today. This post is timely for me personally (and I’m sure many others) and I already feel better about how I plan to confront my feelings. Thank you…

  • Anthony Gair

    Its not that I disagree with this, but wouldn’t folk this far along the track have tons of ‘not giving up’ energy already. Is not the real question, when to take a step back, which may mean starting again on a new project ( with enough steps back).

  • CalebSimpson

    “the harder you work the luckier you get” I totally agree! Pure luck only comes into play on occasion, most of the time the “lucky breaks” are a result of hard work and lots of time. I’m also thankful for the last part of this post that talks about seeking help and mentors. While I do have a hand full of people I seek advice from, leadership/ceo coaching is something have considered, but can’t afford, but after reading this I definitely think I should look into it more and possibly figure out how to make it happen. I could definitely benefit from it.

  • Adam Daniel Mezei

    Peter, GOOD CALL on UNBROKEN. I blew through that book during two long stationary bike rides…

  • petermengo

    Most amazing thing is he’s still alive! 96 – and going strong.

  • Dorian Dargan

    This is awesome.

  • Jack Holt

    Says one of tech’s foremost coaches (so listen to him). Dale, we definitely need to have a beer/coffee!

  • Bart Lorang

    One of your best posts.

  • Citola

    ‘Success is the ability to go from one failure to another with no loss of enthusiasm.’ – Winston Churchill

  • Seyi Taylor


  • Matthew Goldman

    I agree that’s it’s all about confidence. Feeling inspired to write this reaction:

  • oismail

    This is THE post for me Mark. Especially:

    “And back home when you land and come into the office on Monday your
    staff still knows the truth. Your app isn’t getting enough repeat
    visitors. Your churn rates are too high. You have an eCommerce company
    and have to much unsold inventory. Your lead developer quit to join the
    new hot thing.”

    I can’t tell you how many times there’s been that disconnect, people are giving you props on how great your business is doing because you landed a big client or got some press and internally you are freaking out because you know 100 things that are wrong. Think its one of the toughest things to outwardly display confidence while inwardly battling the reality of a startup: where something is always wrong. I wish someone had told me a long time ago that nearly every startup has huge issues.

  • Justin Bastian

    This is like superfood for a fire-belly, a TomTom through the funhouse mirrors. One day I am going to meet you, shake your hand and thank you, Mark.

  • ObjectiveArts

    Oops Meant for the “The Importance of Realism in Startups”

    Mark – Great advice of course. But intelligent humility is striking some times-so nice to hear. I know this is about business but you must be a great Dad.