Advice to advisers: Stop being so nice.


In my first company, I had built a polling application that was doing decently as a social website on college campuses and as a Facebook app.  We were working hard to think of new ways to acquire customers...classic B2C type stuff.  We had some connections to IBM and we started talking with them about how we could sell them on our platform.  Somewhere along the way, we thought that this app could be a great fit for enterprises as well.  Some kind of internal productivity app.  

Let me repeat that.  We were going to sell apps to IBM.

IBM toured me around the company with tons of conference calls.  I made proposals, calculated estimated costs, built mockups.  I worked my ass off.  I reached out to my advisors for help on the sales materials to make them perfect.  As money in my company was dwindling down, I stopped paying myself.  I was on the verge of closing a deal with IBM and optimistic that we would make it through.  We eventually did run out of money, so I funded the company a few more months on my own.

Finally, I pushed for a go/no-go meeting with IBM.  After months of talking and lots of excitement, my IBM contact said they were still interested by wouldn't have a budget for the product.  They said check back next fiscal year.

A sad ending to my little company.  We struggled another few weeks on our B2C strategy.  But we were done.  And it was my fault.

Not because I failed to close IBM.  I know now that we were never going to close IBM.  IBM doesn't do deals with startups.  They were happy to give an eager young entrepreneur a bit of their time, but they never had any intention of writing a check for our services. I should have never gone down that road at all.  Who knows if we would've been successful with our consumer apps, but I can say for sure that we would have had a better chance of success if we hadn't gotten so distracted with IBM.

Now, I know as an entrepreneur, I'm supposed to break down walls and do things that others don't think is possible.  But seriously, was this really the best use of our time?  I had no experience with enterprise software or B2B sales.  Our product wasn't even really a good fit.  AND IBM?!  With 20/20 hindsight, I can't think of a worse company to sell into.  They're big.  They're slow.  And wait for it...they're a fucking tech company!  Why would they ever need our help?

To be clear, this little strategic misstep was 100% my fault.  I pushed for it.  I was naive.  And I paid the price for my suckiness. 

But I got so much help along the way.  Advisers that proofed my proposals, answered my questions.  They mentored me.  They cared about me and wanted me to feel good.

This is hard to say, but I wish they had believed in me less.  Encouraged me less.  Supported me less.  I wish someone, anyone, had put a stop to my foolish ideas.  I'm incredibly confident and stubborn.  I believe I can do anything.  So additional support is kind of wasted on me.  What I really needed is someone that could break through my confidence and tell me straight that I was being an idiot.

It is possible to be this type of adviser.  I now ask better questions of my advisors and explicitly welcome their roughest criticisms.  I gravitate towards those advisers that rip into me with skepticism and challenging questions.  One of my oldest friends has been that adviser for years.  He never believes a word I say.  He pushes me to be better.  I love that.

Now, when I advise entrepreneurs, I try to help in any way I can.  If I don't believe something, I don't hold back.  It's not easy.  I actually would rather be supportive, but I know that the marketplace is not supportive.  It's unfeeling, never satisfied, and totally merciless.  Better to get tough feedback now, rather than fail later.

I've been working with one young entrepreneur that is starting a fundraising round and wanted advice on his pitch deck.  He's waaaaaay too early to be fundraising.  He should be spending 100% of his time building his product and pursuing traction—not wasting time with endless coffee chats and pitch deck making.  He's a stubborn guy (most good entrepreneurs are...) so it was pretty hard to get through.  But, man did I rip into him.  I mean, he came to me for advice, so I wasn't going to hold back.

I felt bad afterwards.  And for a minute, I wished that I had been more supportive.  But only for a minute. This was his response the next day:

Thanks for the advice a few nights ago, it was a much needed smack upside the head.  Thanks for being the voice of reason--a lot of our friends gave us good tips on how to make a nice pitch but you're the only one who was like "what are you doing? why do you need money? stop this!" and it looks like that is probably the right question.

I'm not a dick.  I'm direct.  
(Though I admit, it can be hard to tell the difference)


To all my advisors:
Thank you so much for all your support.  I really do appreciate it.  You're an incredible part of my life and I hope, if you just read this, you don't view me as unappreciative. And the next time you beat the shit out of me with your skepticism...Thank you.

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I would also greatly appreciate introductions to potential advisors.  We're not fundraising until the spring, but I'm happy to 'get coffee' with people who are interested in getting to know us.  

I'm Jason Freedman.  
I've got a sweet-ass new company: 42Floors.  
Previously, I did FlightCaster.
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20 responses
Great post, Jason! I work with a number of startups, and it's really difficult to look at their big, bright eyes so full of hope and tell them that their idea is nice and al... BUT...

I think that one of the things that makes it SO difficult is the fact that entrepreneurs today feel that the need to be disruptive, and that the only good ideas are those that go against the grain. Though you do need disruption to usher in change, you've got to do it in small doses.

All in all though - I agree with your train of thought - advisers need to be much tougher on the companies that they are advising... possibly even the "toughest" so that the company/owner is prepared!

Loved this "Though Love" reminder for advisers....

As someone who has a few small businesses I see to get more than the average number of folks asking for some good advice along the way. I know how much positive energy it takes to just go from just the idea stage to the prototype stage so I always feel pressure to pour on some positive comments and keep them charging forward. Looking back I had a few gut feelings that were negative and I know I held back things that needed to be said. I think there is a fine line from self indulgent tenancies to be the good guy and not want to rain on anyone's parade vs. care enough to tell them the tough love version of the truth as you see it. I have gotten better at it, but takes practice of course and your post was a nice reminder that a true friend never pretends not to see the bugger on your face and with the right tact, do something about it.

Tough love.

If we were only told what we wanted to hear nothing would get done.

The truth hurts, and some people just don't want to bring on the pain.

Thanks for remind us that pain is growth. Just like working out.

Happy to hear that you want the tough love approach. I've always gone that route when working with clients and giving marketing workshops. That's even the approach I'm taking to my new radio show for small businesses in Seattle. But there are times I've gotten flack for it. But entrepreneurs need to hear plain talk if they're going to be prepared for the marketplace. They need to be open to listening. It's not personal, even though it may feel that way. Especially on aspects where they don't have experience or expertise. Now I'm not saying they have to agree with everything, but leave the arrogance at home. No one can know everything, so it's okay to take it sometimes.
As someone who just spent a good deal of time making a pitch deck - this hit close to home. I have trouble admitting there are only so many things I can do and so many hours in the day; prioritization should always be on the front of our mind. Good mentors remind of us that. Thanks for the post.
I wonder though - what would you do if the founder wouldn't take your advice to skip pitching for now? Would you help im with the deck anyway?

I help quite a few people and there is always that thing - guys are doing something I absolutely disagree with (like doing both iOS & Android apps in the very early stage) - how many times to argue with them before giving up?:)

I think i would appreciate someone being more direct too, as ive got older i feel i can handle certain things better now, its often the one person who tells you what everyone else didn't that provides the most help.
Being a dick and being direct are NOT at all similar.

If the best advice in the world is not heeded because you couldn't get the message across in a way that was acceptable to the recipient... then it's not the best advice in the world. You're unlikely to be successful in ANY business if you don't have the EQ to deliver feedback and bad news in a sensitive way.

Oh... and smile more... you'll feel better :-)

Duncan, why put all the responsibility on the adviser? You can still deliver advice in a sensitive doesn't always mean the recipient will take it that way. Communications are rarely simple. Oh, and by the way, may I suggest Barbara Ehrenreich's book, "Bright-Sided: How Positive Thinking Is Undermining America".
Hi Robbin,

Well - you are right, and also entirely possible that the person getting the advice is also an arrogant dick... and that no amount of "sensitivity" can get through to them.

I suppose the point that I'm making is really about coaching skills. If you want somebody to learn... then you need to find the right way to get the change of behaviour that you are looking for. Otherwise you aren't a very good coach.
If you don't care whether that person changes or not - I guess it doesn't matter one way or another how you dispense advice.

Always happy to have a book recommendation - although I'm not unduly worried about any of the things undermining the US as I'm neither American nor a particularly positive thinker.

I did manage to sell to IBM though - which is what attracted me to this particular post.


...not so much arrogant, but probably insecure. And no matter how good you are at working with people, well, sometimes you run into a few that just take you the wrong way. That doesn't make you a bad adviser.

The book rec was really in response to your suggestion that the author smile more. So where are you from? And what's the IBM connection?

Nice write up. Now time for me to find some tough love!
True Robbin - you can't win them all... but the difference between good and bad in this area is maybe 10,000%!

I'm European (From Malta to be specific) and work in Europe, Asia and Africa at the moment.

IBM is one of my clients and I provide them with sales training and a few other bits and bobs. Lots of coaching and feedback involved. I'd lose that contract pretty fast if I didn't manage to convince the clients. (And I have learned this the hard way - it's not a "personality" thing about being nice. It's very much specific to each and every person sitting in front of you)


Duncan...very cool that you work internationally. And thanks for explaining the IBM bit. Yes, every client is different, and consulting by its very nature means tailoring the communication to each. And I agree, it shouldn't be a "personality" thing, but we all being human, it sometimes gets in there. And that's where the magic can sometimes happen -- a real connection.
What a great post. It's always a thin line between being a supportive mentor and the skeptical bloke who kicks you in the teeth.

I worked for many years as a press photographer. My first picture editor told me "I don't want to know your problems, just give me the picture". He didn't care how hard I worked - just if I got the results. If you can see how hard the guy has worked on that new biz plan/strategy/deck - it's hard (but essential) to say if it's delivering or not (no matter the blood, sweat and tears they have given).

Later, when I ran a business I had an angel investor that I took no notice of, VCs who were frustrated when I sacked their non-executive chairman - but I did take some of what they said on board (and delivered them a win in the end). I was a typical, badly behaved, knows better, can run through walls entrepreneur.

I look back and all the home truths they told me, kickings they gave me helped keep the business in the right direction. You are right, it's 100% your decision - and the kickings help along the way. Honesty is the best policy - and I think well of these advisors/investors (in retrospect!)

Very good. Although I wish mentors would stop giving advice on pitching, product development, etc and just focusing on making sure the entrepreneur just understands how to formulate a hypothesis and then test it.

Too many entrepreneurs just follow mentors blindly without verifying facts with the customer.

One challenge is that there is a natural selection bias in the selection of advisors. Most people pick advisors who are supportive of their project and the advisors that tend to be most active are those that are most positive about the project's potential. The trick is seeking out advisors who are both willing to tell the truth and also spend the time advising someone on something that they may not consider the greatest idea in the world, at least at the outset.
Great post! I've been on both sides of the equation, and you're absolutely right. Entrepreneurs can be killed with encouragement...
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