Embrace Your Losses – They Will Make You Stronger

Posted on Nov 25, 2010 | 65 comments

Embrace Your Losses – They Will Make You Stronger

This is an updated post from my ongoing series on Startup Advice that I learned from founding two companies.  frustration

I HATE LOSING. I hate it.  I really, really, really hate it.  It chaps my hide.  It rips at my core.  I don’t get over it easily.  I lose sleep.  I fucking hate losing.  It’s not so much the actual outcome that I hate – it’s the process.  The fact that I lost when I should have won.

I think about it for months, often years.  But I embrace losing.  It is how I learn.  I relive the moment so many times over in my mind wondering if I could have done this differently or if I shouldn’t have said or done this or that.  I talk to trusted sources about it.  I ask for feedback.  I hate losing.  I don’t want to lose next time.

I believe that it is part of the DNA of an entrepreneur – being so competitive that you’re practically sick when you lose.  It’s what makes you stand out from the rest.  Entrepreneurs are neurotic about it.  They’re competitive.  It’s the one thing I miss having switched from player to manager – I love the joy of winning and of competing.  It is never as rewarding when you’re the coach (but coaching has many other benefits 😉

Don’t get me wrong – I’m not a sore loser.  I don’t break tennis rackets, cry foul, fall over like an Italian soccer player or work the referees.  Quite the opposite.  I’m usually quite a gracious loser.  I don’t hold grudges.  I move on.  I keep my competitors as friends and those that didn’t choose me or my product as friends, too.  But I never really get over it.

I’m not talking about garden-variety losses – that sort of loss I get over in a couple of days or weeks (but you don’t want to be around me that evening for sure).  I’m not even too bothered by the occasional deal that got away.  I’m talking about the hard fought battle.  The one that you thought you had.  The one you were counting on.  I’m talking Tom Watson at the British Open or Andy Roddick at Wimbledon.

On Losing in VC

Last year I lost a deal in a company that I wanted to invest in and that I thought I should have won.  I was angry – mostly at myself.  Rather than blame the team that I thought should have chosen me, I became reflective.  They were in LA and I was in LA.  They had a prominent NorCal investor already so I thought a SoCal lead would make sense – that I could help them in a more hands-on way.  They had agreed!

I had lost a previous deal where the team said they liked me but didn’t know my partners well enough so I promised myself never to let that happen again.

So I organized a team dinner with all four of my partners and all three of their founders.  I wanted to be sure that they knew how much all of our partners loved what they were doing with their company.  I wanted to be sure that they felt they knew all of my partners well so they could see why I joined up with them in the first place – they are smart guys who have a 20-year track record of winning.  15 companies North of $1 billion exit.  And they are normal, down-to-earth people as well.

After dinner on a Thursday night I thought we had the deal and that the team knew how hard I would work on their behalf if I were chosen.  By Monday morning after their board meeting in NorCal I didn’t get a return phone call.  I knew what this meant.  Good news always comes quickly, bad news takes time to simmer.  By the time I got through to the guys on Tuesday we had lost.

I knew that the, “I’m really sorry” message was coming.  I embraced it with honor and didn’t give them a hard time.  But I obviously asked, “Why did it happen? I need to learn for next time.”

There were two main reasons that I could distill from their kind words of solace:  1) the existing NorCal investor didn’t know me well enough & 2) the new NorCal investor had a good knowledge of and presence in China, which they believed would be critical.

I decided to put both of those issues to bed in 2010.  I came several times to NorCal (where I grew up, actually) and went and met several partners from each Silicon Valley firm.  I didn’t want this to happen again – that people didn’t know me.  I also made several trips to New York & Boston.  Next year I’m going to spend time in Seattle and Boulder in addition.  I realized that it is not enough to know one partner per firm and it is not enough for only the management team to like you.  VCs have a seat at the table in deciding future investors.

I also spent two weeks in China and vowed to make it back frequently.  China is indelibly an important part of the future of the global technology system.  Although I had lived and worked in more than 10 countries – it wasn’t good enough. I didn’t know the one that mattered most to their future.  And for my own good I vowed to have relationships in China and knowledge of the local markets.  I’m not looking to invest there – I’m looking to understand the trends, the people, the innovation, the regions and how China can become an integral part of any of my portfolio companies as they scale.

I know I won’t win every deal I want to in VC.  There are other great VC’s in SoCal and there is always the allure of the NorCal guys flying down and talking about how they invested in Google, Facebook, Yahoo! or eBay.  But I will learn from any deals that I want to do and am not able to do.  I will embrace my losses.  May they be few and far between.  I can’t afford more sleepless nights.

This company is back on the market raising money again.  I love the area and the team as much now as I did a year ago – probably even more now that I know them better and have seen them perform.  I’m dropping everything non-portfolio related in the next few weeks and setting my sights on righting my wrong.  One great thing about losing is when you get a second chance.  I hope the next chapter will be written by the victor.

Make sure you learn your lessons from losses.  Specifically:

lockerroom1_original1858421. Ask your customer why you lost. Tell them that you’d like to learn so that you can improve.  Promise you won’t be defensive or try to change the decision.  Best to ask after the dust from the decision has settled.  Ask multiple people involved with the decision.  Be gracious.  Write things down.

2. Discuss with your team – do your post game analysis.  Don’t ignore your losses.  Don’t blame the people involved with the loss.  Don’t accept your internal team’s answer of why you lost – hear it for yourself.  Make sure that you hear all of your team’s perspective.  Draw your own independent conclusions – even if they are different from other people’s point of view.

3. Triangulate. Who else was involved with the decision?  Were their consultants?  Can you discuss further down the line with your competitor?  Do you have friends on the inside?  The clearer picture you have of why you lost the more you’ll learn for next time.

4. Learn.  And don’t make the same mistake twice.  Obvious, but I find that some people just never learn.  I read this post from Marc Hedlund at Wesabe on why they lost to Mint.  It’s one of my favorite blog posts.  I don’t know Marc but now I feel I want to work with him after reading this.  I had planned to blog about it at the time but I waited 2 days and the whole world blogged about it so I didn’t pile on.  If you never read it, please do.  It’s brilliant, reflective & humble.  And I think he’s right that Mint never solved the problems the industry wanted to solve.

Looong Appendix (only for those interested in reading another story about losing a sale & key lessons):

A personal story of losing a sale that haunted me for years

soccer loss

In the 2003/04 timefame I was living in the UK and running my first company.  I had been competing to win a contract at Thames Water, the largest water company in the UK.  They were looking for a collaboration tool to manage all of their large water development projects.  The initial contract was worth about $500,000 and the whole value of the contract would have been worth a couple of million over the years.  I was working hand-in-hand with my close friend and associate Stuart Lander who was running our UK office and with one of our local sales reps.

We had initially been told that we had no chance because they had previously purchased Documentum and it would mean changing the system entirely.  They had a team trained up in Documentum and we certainly had enemies from the inside.  But we worked the account tirelessly for months.  We helped the write out their requirements for a system.  We met everybody in the organization.  We had every reference client we worked with call their senior team members (we had already won a major project at Scottish Water, Anglian Water and another at a large water company in Paris, France).

There were about 8 initial contenders for the work and in the end it came down to just 3 of us.  As the founder & CEO I personally went and met with as many people at Thames Water as I could.  We felt this was a marquee account and one that would help us take our collaboration tool global as Thames owned assets all over the world.  Winning the contract meant that we would hit our quarterly revenue figure and be in good position for our annual sales target.

And then the news came.    A woman named Trish Hannon called me with the good news that we had won the project.  I was to tell noone until the contract was signed.  I immediately put a full team on contract management and another on drawing up an implementation plan.

DefeatI later learned one of my biggest lesson in sales.  You are most vulnerable right after you have won a deal.  It is when you’re competitors have nothing to lose.  It’s when the people who are part of the decision making process who don’t support the decision seek ways to undermine you.  That is when you potentially become complacent.

Two weeks after winning the deal and well into implementation planning we released a new version of our software.  We had made the decision that we would no longer be supporting IE v 5.5 (we would support 6.0 and 7.0, which was in beta).  Even Microsoft publicly said that there were security flaws with 5.5 and that people should upgrade.   But Thames Water was still on version 5.5.  We assumed they would take our advice and upgrade.  We had discussed this with Trish.

An internal resource inside Thames Water used our upgrade and lack of 5.5 support as a way to re-open the decision.  How could a company like ours be so callous as not to support their software (even one more than 4 years out of date)?  Did we really have good change management procedures if we were willing to launch products without backward compatibility. And so on.  They decided to re-open the competition for 3-4 more weeks.  I knew THEN that we had lost.  We fought hard to stay in the game.

They hired a consultant to help them with the review.  They stopped allowing us to contact them directly.  The momentum had shifted.  Something happened and it was clear to me that this IE issues was just a smoke screen.  Somebody had gotten to somebody senior in the Thames organization.  It just so happened that the consultant they hired to chose a software vendor worked for a company that had owned one of our competitors.  It was a tiny little collaboration company that only had a presence in the UK (and therefore couldn’t meet their international needs).   And surprise, surprise the decision came back 3 weeks later than none of the preferred 3 vendors had won but rather this tiny little competitor owned by the consulting company charged with doing the review.

Outrage.  Scandal.  Surely inside Thames they would see it for what it was.  Given that it was a public tender the chairman of our board had encouraged us to think about launching a complaint with the UK government agency in charge of such reviews.  We talked with lawyers.  We felt totally deflated.  We decided it wasn’t worth the fight.  We licked our wounds and moved on.

I am still not over that loss.  I sometimes call Stuart and we recount what happened.  But that loss was really important in my career.  It taught me a lot of lessons.  We spent enough time dissecting it to really learn.

Here are my take aways from the loss:

1. In a sales campaign you always need to call as high as you can.  If you don’t, your competitors will.  If you don’t know them, somebody else does.  They may not overturn decision, but they sometimes do.

2. No deal is ever done until the ink is dry and the money is in your bank account.  Never take your win for granted.

3. You are most vulnerable right after it has been announced that you won (I will write a separate post on this). This is the most important lesson I learned from this experience.  All other lessons were sort of obvious.  This one was eye-opening.

4. We in the tech world extol the virtues of lots of product releases and rapid innovation.  I hear Silicon Valley firms bragging all the time about how often they release software.  In the consumer world, maybe.  In the corporate world this strategy is flawed.  Many large clients prefer stable technology and no changes – even sometimes when there are known security flaws.  When I was at Salesforce we launched a new version of our UI.  We gave users the choice to upgrade or keep with the classic UI.  Years later 10% of users were still on classic.  Go figure.

5. In every deal where you have serious competitors there is always somebody on the inside against you.  You need to find out who that is and neutralize them.

6. No matter how much your customer tells you that they love you and that they favor you it is possible they are telling other people the same thing or some variation of this.  (you would have thought I would have learned this lesson in high school 😉

7. No matter how much large clients tell you they want transparency in pricing, they always seem to fall for the same old trick.  Competitors price low to get in the door and then nail them with scope control, change orders, product extension costs and other hidden items.  You can try to convince them of your “pay no more once you’ve signed up” model but they fall for the other guy’s pitch every time.  Low numbers are sexy.  I stopped trying to win this argument and chalk it up as some sort of human condition that I can’t change (like thinking that $14.99 = $14).

8. Time is the enemy of all deals.  If you have a chance to close something – don’t let it drift.

9. Losing sucks.  But at least it has made me a better competitor.

  • http://www.impercode.com Mantvis Umbraziunas

    Very good post :)

  • http://www.repeatablesale.com/ Scott Barnett

    Great post and impressive to see you lay out your soul – it's hard to admit defeat! One thing I noticed is how you learn from lost deals – which I always try to do. At the same time, you can't be all things to all people – while it's always hard to simply realize the other side “doesn't like me” (as you alude to with your high school analogy), there will be deals where the other side just likes somebody better. Even if you introduce them to all your partners, become an expert in China, know every VC across the country. I'm not saying those aren't good things to do – I'm wildly impressed that someone with your street cred feels they need to “shop” themselves – but they aren't guarantees of success.

    I remember a deal very early in my career where we sat at dinner and the decision maker told us “the deal is yours”. We celebrated that night, and told the entire team when we got back to the office. It unfolded almost exactly as your Thames Water deal did, in alarming detail. Thanks for the memory :-)

    Have a very happy thanksgiving.

  • http://www.kirillzubovsky.com Kirill Zubovsky

    Thanks for the post. I got some validation that it's okay to obsess about loses as long as it helps to win at the end.

  • http://twitter.com/miLifemap mi Lifemap

    Great post! Made me think of this Sydney Crosby commercial after losing the Stanley Cup. The next year, they won.

  • Matt Cameron

    I think that the sport analogy is perfect here. I have been connected to elite sports people for years and one notable difference between amateurs and the elite is that the elite are overtly gutted when they don't get the result. It is the elite athlete that walks off the field of competition crying and wanting to smash something. The key is that they then obsess about analyzing what went wrong and they build a plan to fix it, starting immediately – if not sooner. :-)

    This abhorrence for losing is what drives them to get out of bed at 5am for training 6 days a week and perform at their peak day in and day out. I look for this type of determination and competitive aggression in my business partners because I know that they do whatever it takes to win.

  • http://twitter.com/GKedzierski Grzegorz Kedzierski

    I agree that learning from failures is important but it only tells you what you shouldn't do – it doesn't teach you how to be successful (and I doubt that failure itself will increase your chances of succeeding the next time).

    Anyway I also believe embracing failure is a key to success. I know so many smart people that will never succeed just because they're afraid to fail.

  • http://www.davidblerner.com davidblerner

    Wow… this is a powerful (and at times haunting) post which dredged up some of my own painful memories.
    Also, several of your refrains and reminiscences conjured up some flashes of DeNiro's performance in Cape Fear… remember some of those scenes? DeNiro telling Nick Nolte “Counselorrrrrr, you're going to learn about loss” in that unforgettable voice? He sure was right.

  • Villalba1000


  • http://donaldryan.net DonRyan

    Terrific post. I am also a very sour loser. Hate it with a passion. Thanks for your transparency on your losses and follow-up to prevent them from happening again.

  • Marcin_Wozniak

    Take away no 7 – I can see this much to often in large IT software deals, with change requests being 50% and upwards of the original contract value.

    Very powerful stuff here Mark – thank you!

  • Kylepearson

    “You need to find out who that is and neutralize them.” You're insinuating something right? You have to call a guy, who knows a guy, who has a friend who takes care of these kind of things quietly? :)

  • Fashionmoves

    As someone who is new to 'business' there were a variety of valuable pieces of information here. A question though if I may.

    The work I am pursuing would be considered disruptive by some, not worth taking time to look at by others and badly needed by the hundreds of thousands of people around the world who understand and want this product badly.

    It seems that VC's are willing to spend $50,000 or more during negotiations on a large deal only to loose it. Yet they are not willing to consider that a $25,000 loan could be completed in 3 or 4 days and that could cause a revolution within a specified industry.

    I am sure loosing sucks in the situations you describe but what of projects that are unique, have proof of being needed and only need relatively small amounts of invest.ent? Loosing on these is much harder.

    Anyone willing to come along on my ride?

  • http://www.blogtalkradio.com/fashionmoves Fashionmoves

    As someone who is new to 'business' there were a variety of valuable pieces of information here. A question though if I may.

    The work I am pursuing would be considered disruptive by some, not worth taking time to look at by others and badly needed by the hundreds of thousands of people around the world who understand and want this product badly.

    It seems that VC's are willing to spend $50,000 or more during negotiations on a large deal only to loose it. Yet they are not willing to consider that a $25,000 loan could be completed in 3 or 4 days and that could cause a revolution within a specified industry.

    I am sure loosing sucks in the situations you describe but what of projects that are unique, have proof of being needed and only need relatively small amounts of invest.ent? Loosing on these is much harder.

    Anyone willing to come along on my ride?

    Ruth Clark fashionmoves@earthlink.net

  • Rohan

    Awesome post! This was very inspiring – thanks a lot!

  • http://twitter.com/suyogmody suyogmody

    Great post! Like all of your other posts, very conversational and detailed, and yet manages to bring the point across.
    Most of the lessons learned are consistent with any sales process, yet what struck me is #4 under your appendix. I'll spend some time thinking about how this relates to the product management and prioritization techniques. Also some good thoughts on a Quora thread – http://www.quora.com/What-are-the-best-ways-to-prioritize-a-product-and-feature-list

  • http://twitter.com/nepalsites Roshan Joshi

    well said. for me, losing hurts but its not about losing or falling but rather about getting up & start kicking again.

  • http://www.gazaro.com Alexander Rink


    Great post, as usual.

    I agree with the content of your post (and have experienced similarly painful losses myself), but for what it's worth, I disagree with your title: I don't think anyone should ever embrace losing. Rather, as your content implied, we should embrace our losses and setbacks, and learn everything we can from them to minimize the probability of our losing again in future. Losing, on the other hand, is something to be abhorred and avoided in every way possible.

  • http://bothsidesofthetable.com msuster

    Thanks, Scott. I agree with you. In my post I kind of acknowledged that I know you just won't win some deals. But the ones that burn to the core are the ones that you thought you won – that you should have won – and didn't.

  • http://bothsidesofthetable.com msuster

    True. I think the sports analogy is a good one. Hope things are going well for you. Love the reference to “gutted” than any Yanks reading the comment won't get! 😉

  • http://bothsidesofthetable.com msuster

    Good point. Analyzing losing in and of itself is not the key to winning. But not analyzing losses is probably key to not winning some competitions that you should win.

  • http://bothsidesofthetable.com msuster

    DeNiro's the best. And that was one creepy film!

  • http://bothsidesofthetable.com msuster

    hehe. well, not exactly. I have a future post on how to deal with the enemies at your customer. You have to neutralize them. Watch this space – hope to publish in next 3 months.

  • http://bothsidesofthetable.com msuster

    VCs generally don't spend any external money until they have a deal agreed. VCs will invest small amounts of money on teams that they think are building big ideas. The problem is that we get thousands of pitches / year and most think their idea is the big one. We can't back all of them.

  • http://bothsidesofthetable.com msuster

    I think that so much of the wisdom in Silicon Valley applies to consumer tech but people apply it to enterprise tech where the rules are different. Many smart people who aren't experience in the enterprise never realize this. Those of us that are learned the hard way.

  • http://bothsidesofthetable.com msuster

    Ok, if you want to interpret it literally I agree with you. I think I chose the title more to make the point that too many people prefer to move on from losses rather than be reflective. If we embrace the times that we do lose as a way to learn then I stand by my title. But your point is how I feel – I abhor losing. For sure.

  • Bhavesh Shah

    Great Post!! Just one query related to #4.

    What I understood is that building MVP, iterating and releasing new features in an enterprise world doesnt work given the preference to stable technology. Please correct me if i am wrong.

    What should be strategy there if you are bootstrapping but your product is for large corporates?

    We are working on an invoicing product which is for smaller corporates, say upto 200 employees. Once we have a base of clients, we plan to create a back end for banks for certain additional processing. Target is to approach the banks once we have a reasonable client base.

    What do you think is the correct strategy given that we are talking about an offering for small corporates as well as large banks?

  • Chinaccelerator

    “No deal is ever done until the ink is dry and the money is in your bank account” would deserve an entire post in its own. Crazy way of loosing but happened so many times after parties gave each other a high-five!

    See you again soon in China!

  • jordipuigdellivol

    Hi Mark! Thanks for sharing a bit of your life and specially all the learnings you got from those hard experiences.
    So much knowhow embedded in your lines!

    Jordi Puigdellívol

  • http://www.gamesbrief.com Nicholas Lovell

    Do you really think that being competitive is the be-all and end-all of being a good entrepreneur?

    Competition with others (and hating losing) is one aspect of being really good. Others include beating yourself (rather than others), being a knowledge expert (deeply understanding something), having the social skills to close the deal.

    Your post suggest that you would only back someone who the competitive spirit of a jock. Is that a fair representation of what makes a good entrepreneur? Would you have back someone who, in a squash game, didn't care if he or she won or lost?

  • Srikanth Achanta

    While reflecting is good, I think one needs to be a bit careful from learning too much from mistakes, taken too far it could be a reason for your next failure.

    If a center forward on a soccer field misses a couple of chances just 5 yards from the goal and tries to learn too much from it. He might miss his next 5 chances with hesitation to shoot which is his natural reaction.

    I donno if i worded my thoughts properly but i think you can get the gist of it. :)

  • Jos Burger


    Rule 10. Bring all your people in the sales process. Let the techies talk with the techies, sales guys with the purchasing dept., your fin/adm guy with their legal and finance people. Make sure you cover everybody who is involved. This will not eliminate the risk of losing, but it will surely increase the chances of winning the deal.

  • http://twitter.com/chrismottes Chris Mottes

    Your point 7 about large companies falling for the low initial pricing when it is clearly going to go up through scope control etc has been a challenge for me many times. I still have problems with this misleading approach and find it hard to accept. But as you say, it is a human condition that cannot be changed no matter how illogical…

  • http://naamanetworks.com/ David Bloom

    Unstated in your first part is that winning sometimes means wearing your heart on your sleeve. Go for it, sing out loud. The startup you are wooing obviously knows how much you want them. This makes you vulnerable on one level- not just a missed deal but a broken heart- but love is powerful. Everyone wants love. A great differentiator and the foundation of a good relationship. Bravo for letting it all hang out.

  • http://hdemott.wordpress.com Harry DeMott

    I like #4 – Learn. Yes, always try and learn something from your mistakes.

    However, I would also add another comment: call it #4a – Teach.

    Teach, not only your colleagues so that you all learn, but also make sure to follow up when you have lost to teach them to some degree why they have made a mistake. So in the VC example you gave – hopefully you have been in touch with that company constantly since their last round – teaching them why having you as a partner is and was such a great idea. You say they opened up a new round of financing – a real win would be a direct conversation with you and no one else! I know, unlikely to happen, but if you really pursued them and taught them your value – and the value of your team – it would be more likely.

    My partner and I always used this technique in investment banking. While we won a lot, we didn't win everything – and when it was important to us – we would just stay in touch with useful advice – offers to do stuff for the company to the point where we hopefully taught them that they had likely made a mistake the last time around – and reversed course the next. It worked some of the time – and we never lost business as a result.

  • http://bothsidesofthetable.com msuster

    MVP can work for enterprise. The key to understanding enterprise is knowing that they don't necessarily want a ton of feature changes so you have to make new features modular and give them the ability to turn on when they're ready.

  • http://hdemott.wordpress.com Harry DeMott

    One other comment – now that I've gotten to think about your theme – sometimes losing isn't that bad and may make you far better in the future.

    Let me give you a few examples:

    1. Back to banking days (I was an analyst but in the 90's we could work as bankers effectively). We were obsessed – Ahab like – with super serving Clear Channel – the absolute leader in our business. We won their first mandate for a investment grade bond – and the market ultimately priced it 3 basis points behind where we said we could do it. We told the bank to eat the 3 basis points. They didn't and Clear Channel was pissed – and told us to call them in a year. While my banking partner was apoplectic, I viewed it as an opportunity. No matter what we did, we weren't getting any business from them for a year – so why worry – why not focus greatly on every other company in the space. We did, and the next year was our most profitable. Sometimes losing when you are obsessed is a blessing in disguise. (A year went by and we went on to do a ton more with CCU anyway)

    2. Just read the Vanity Fair excerpt on Prince William and Kate Middleton. Lots of on again off again etc… She gave him an ultimatum, he said no and they went their separate ways. Rather than sulk, she seemed to get right back out there – and ultimately showed William what he was missing. She won by being a good loser.

    3. I platy a ton of paddle tennis (platform tennis to some) and sometimes I just run into players that are just much better than I am. While no one likes getting their asses kicked – I actually enjoy playing with and ultimately losing to better players – because they expose my every weakness and I see strengths in them that I can emulate. I get stronger by losing. Over time, I'll get closer to them.

    I completely agree with your assessment about losing when you think you should win. There's nothing worse than that. Missing a trade. Not investing in a company where you think you are a perfect fit. Losing to an inferior team in sports. Basically, beating yourself.

  • http://bothsidesofthetable.com msuster
  • http://bothsidesofthetable.com msuster

    I do think that being competitive is an important attribute but not the only one. I wrote a series of posts on the topic. They are here:


  • http://bothsidesofthetable.com msuster

    It's not about “over thinking every error you make” but when you lose a game you should have won. Then you look at the game film to see if there is anything you can learn. This happens after every game in sports. I'm just telling people in business to do the same.

  • http://bothsidesofthetable.com msuster

    agreed. i was just talking to a company about this on wednesday!

  • http://bothsidesofthetable.com msuster

    It pissed me off for years but then I realized that I can't change human behavior so I had to change myself and accept it.

  • http://bothsidesofthetable.com msuster

    We tried to tell every early customer how important they were to us – and we meant it. In VC I still tell companies I'm looking to invest in the same thing. I'm very explicit about this.

  • http://bothsidesofthetable.com msuster

    Agreed. And yes, this was and is my approach.

  • http://bothsidesofthetable.com msuster

    I agree with numbers 1 & 2 – it's how I think about life.

    But I especially love comment 3. I feel the same. You never improve by beating up on players worse than you are, you improve by playing against people who whip you.

  • David Bloom

    One of my friends & family investors (a successful entrepreneur) told me the best brochure is a happy customer. That simple statement has deeply effected our product road map. We are now pouring resources in to our existing clients instead of hunting for the next elephant. For one client, we even have a Christmas present planned in the form of a special product feature.

    That said, some people would argue it is different telling an existing customer that you love them, and saying the same thing in a negotiation. I am not one of those people. I even told one prospect I was going to make them so happy I would never pay for marketing again- they would drive word of mouth. That was our first meeting. I hope that wasn't overkill. Deal is still pending.

  • philsugar


    Its the same as giving your absolute best price upfront and expecting to not have to negotiate.

    Just kills me. I've lost a deal where in retrospect I know if I had priced it 20% higher and come down I would have won. Yes you could say we were being used as “column fodder” but I really believe the client gave the competitor our bid and they agreed to match it, and the fact that we wouldn't come down meant they were paying “full price”.

    As much as people said they want to just see a fixed price for a car, they want to negotiate.

    I love going through sales losses. I won't hire a salesperson unless they can recount in great detail a deal where they got their ass kicked. If you are playing you are going to lose, it doesn't mean you have to like it but you have to realize what to do when you do.

    This is why I hate the “everybody is a winner” attitude at school. My daughters Principal was appalled when she stated “my Dad says there is one winner and after that comes the first loser”. I had a long talk with the principal explaining that the best time to learn about losing is when it doesn't really have any consequences like in kindergarten. If your first experience at losing is when it something important like you figure out you aren't going to get into the college you wanted, it has to be crushing.

    Its also what worries me about first time angels throwing out money that they really don't think could ever lose.

  • Vlad Azimhodjaev

    haha. I liked the comment about Italian football players. Very true!

  • Dave W Baldwin

    For what it is worth David….I checked out your site and really like your concept. Nice to see others that see the other side.

  • Dave W Baldwin

    Great post. You had to be gnashing your teeth over Thames, running into the brick wall associated with big corporate. Even if you'd have proved the security issues, they still would have had to have a series of meetings.

    Way back during the fun days of Group Health, I showed a product to a medium sized company using an Insurer with better rate increases and a track record…in the end, I won out on the proof, but they ended up using their agent to do the switch.

  • http://twitter.com/hisern Heidi K. Isern

    I really enjoyed this post, especially after having a recent client proposal evaporate. There are life lessons here as well, learnings that extend outside of the board room walls. As a part-time writer, I can see an analogy to book deals/article submission. (i.e. did I really assess competition/what else has been written to ensure I had the right angle). My job seeking friends can apply some lessons to their interview acceptation/rejection process. And once can even use the learnings in relationships…

    “In order to succeed you must fail, so that you know what not to do the next time.”
    – Anthony D’Angelo –