Advice to advisers: Stop being so nice.

This post reminds me of a favorite passage from Lord of the Rings, when Frodo is debating whether he should wait for Gandalf in the Shire, or press on:

“… The choice is yours: to go or wait.” [Gildor said.] “And it is also said,” answered Frodo, “Go not to the Elves for counsel, for they will say both no and yes.”

“Is it indeed?” laughed Gildor. “Elves seldom give unguarded advice, for advice is a dangerous gift, even from the wise to the wise, and all courses may run ill. But what would you? You have not told me all concerning yourself; how should I choose better than you? But if you demand advice, I will for friendship's sake give it.”

The problem is, most of your advisers probably didn't know and, more importantly, couldn't know if the IBM sale would pan out. If they said stop, and you did, and failed anyway, what if they felt bad at whether the IBM sale might've worked?

The world is big and unpredictable and replete with stories of people advising others that something can't be done or shouldn't be done that way, only to have the advisees ignore the advisers and do great things. Hell, see this post: http://matt-welsh.blogspot.com/2009/02/how-i-almost-killed-f... for an example of well-meaning advice that, if taken would've been wrong.

It took me a while to understand the full benefit of people's criticism. My team's initial idea was a to build a mobile product that essentially focused on everything and added a ton of features, thinking that we'd get users from being so ubiquitous and awesome. After hearing the same "you're not focused", "how can you get users" criticism from many in the industry (including multiple YC partners), I finally got it through my head that maybe I couldn't impose my naive vision on the world just because I believed it was powerful.

However, its just as important to never stop thinking about your world-domination vision. I'm sure every one of the most successful tech companies in the world has heard all of the same criticism from well-meaning advisers along the way. Start with a focused smart plan, execute it well, and don't lose sight of the ultimate destination (which may change along the way too as you learn more).

"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. "

Just as you used to do, most people do not listen when criticized harshly.

You can try to blame your advisers for not telling you to avoid IBM, but in the end, it's still your fault and not theirs. In fact, they probably tried to tell you that, but you didn't want to hear negatives.

It's good that you can hear them now, but that still doesn't help most other people, and those advisors still have to deal with those people.

The reason people don't typically act this way is that anyone who tries to give honest advice quickly realizes than in 90% of cases, the person seeking advice doesn't want to be challenged. Especially budding entrepreneurs, who are often precariously balanced between wild optimism and despair. It's very hard to stay positive when someone points out that your baby isn't quite as beautiful as you imagine.

This guy is being way too hard on himself. Running out of cash is hard and painful enough, no need to unduly heap blame upon oneself. If people at IBM were talking to him about a deal, then they weren't doing it to coddle his startup or be nice... trust me, if people aren't interested they won't be shy about saying no. I think he got caught out by the slow-moving bureaucracy of a big firm... too bad for them, their loss. As for IBM being a stalwart of the tech industry not needing help from a brash young startup, isn't that exactly how Microsoft got its first big contract?

This wasn't a case of needing harsher advice (too many people are addicted to self-flagellation, as if crushing your own dreams was a sign of maturity) but a case where a fledgling company took a big risk. Risks are risks, there's no way to to apportion blame or change course in hindsight. This just as easily could have been a post thanking his many mentors for their sound advice and encouragement that saw him through to getting his first big sale to IBM. Just because the other party in a negotiation is a big corporation that lumbers along and takes forever to make up its mind, there's no need to berate oneself for not having tried harder or seen x,y,z in retrospect. I say good on him for having gone balls to the wall to bring his vision to life, and good luck with his current venture. But the lesson here is not about advisers, in my view, it is about caution when dealing with massive organizations.

I don't know who your advisers were, but there's an alarming trend in tech/startups right now where anyone associated with a startup becomes classified as a mentor. Some of the accelerator programs sprouting up have some very speculative names as "mentors" -- people who just seem to have a few years of experience, perhaps mid-level experience, who haven't built their own company, haven't led their own go-to-market strategy, and whose advice on product is no better than you'd get on any forum.

I'm not sure how this matches up with your previous article, http://www.humbledmba.com/dont-give-bullshit-advice , that made the point: "Don't tell an entrepreneur whether you think his idea will work. You don't know. You have absolutely no idea."

Either you give advice about what doesn't work, or you don't... you can't do both.

As an advisor (on the giving side) and an entrepreneur (on the receiving side) I totally agree with this.

It's tough because people are nice, but as an entrepreneur, I learn the most from the negative advice I have gotten from mentors (I've been ripped apart many times).

So now, when I give advice, I give my true honest opinion if I don't think their idea will work. I just preface with it saying, look, this is only one opinion, and not to take it personally.

And when I get ripped into, I always listen and ask questions, but I don't necessarily let it discourage me.

I think you can always tell by people's expressions if they are holding back. If you think they are, you should ask them: "It seems like you have some reservations about this, what are some of the risks you see?"

With that, you'll be able to get more insight, and you just have to remember that there's tons of risk, it's just up to you to decide how risky each situation is (and how to mitigate that risk).

I totally agree. Advisers should be more like Asian parents. "Western" parents (much like "Western" advisers) start with the premisse that their children's self-esteem is fragile and therefore constantly try to reassure their children about how good they are. While Asian parents start with the premisse that their children's self-esteem will build up with improving performance hence are consistently critical and pushing their kids to improve. here's a link to different parenting styles - http://proto-knowledge.blogspot.com/2011/01/asian-vs-western.... I think advisers might learn a thing or two about "parenting" startups from it

I believe honesty is absolutely essential for a good mentoring relationship. But it's sometimes counterproductive to be too blunt or too harsh. One way mentors can help the entrepreneur without coming across as negative or critical is to ONLY ASK QUESTIONS. Don't give advice. Don't lecture. Just ask a series of good questions. More often than not, while answering one of those questions the entrepreneur will have an aha moment on their own. Good questions from a trusted mentor have provided many a helpful knock-up-side-the-head for me -- without things getting adversarial or emotional.

I've actually found it's quite hard to get negative feedback from most people. I've literally heard one person shush another person who was trying to say something negative about what I was building - when that was the exact feedback I really wanted. I bet if I looked closely and in retrospect I could figure out what people didn't like after it fails, but that doesn't help me now, I wish people were more direct and honest.

I might be foolish, but being able to say that you were in intense negotiations to have IBM acquire your app is still a HUGE deal.

Even if it was not successful, it is a great story and demonstrates great potential. Congrats on your failure!

I always ask people "what's wrong?" and "tell me what sucks about it?" or "why won't you use it?". Positive feedback rarely spawns growth. Criticism and negative feedback is PURE GOLD.

As an advisor, this is tough advice to follow, but if you don't, you aren't provided real value.