How Not To Start A Relationship

In the last month I’ve had the chance to make about 50 new friends. I’ve suddenly become very popular with investment bankers and have been on the receiving end of over 50 emails that look something like the following:

“We met once a long time ago when I was with firm X. I’m now at firm Y. We are the blah blah blah best at blah blah most successful blah blah tied into blah blah working with blah blah blah connected with blah blah blah. Congrats on all the success at Company W. We are very interested in talking to them about blah blah strategic blah blah – can you introduce us to high-profile-CEO.”

At first I felt compelled to respond as part of my “answer every email and try to at least be polite / responsive to everyone” approach to life. After a few days, I started getting annoyed when I realized I was simply viewed as a conduit to an introduction. When I saw a few similar emails to my co-investors in at least one company, I realized that there was a complete lack of sincerity in many of these emails – it was no different than a random salesman emailing me asking if I wanted to buy a random widget.

Now, I have several good friends who are investment bankers and we have a handful of trusted ibanking relationships and folks who are our go-to ibankers. These are people who have developed a long standing relationship with me and my partners, have worked with us in good times and bad, and have always been reasonable and thoughtful about their fees, especially in situations that didn’t work out.

It amazes me that 50+ people could suddenly come out of the woodwork in an effort to “build a new relationship that’s not really a relationship” thinking it would give them an opportunity, or even an advantage, in the context of a set of hot companies.

When I think about the relationships I’ve developed, whether it be with investment bankers, LPs, co-investors, or anyone else, they evolve over a period of time. They don’t require boondoggles or fancy things; they require sincerity and substantive interaction over a long period of time. Then, when there are moments of opportunity, these are the people that I go to (and hopefully who come to me.)

There suddenly seem to be an abundance of “transaction relationships” out there. Entrepreneurs beware.

  • I wonder about this sometimes. When I go to networking events for example, I meet a lot of people, and many of them are awesome people I would actually genuinely like to be friends with and go get a cup of coffee or a beer and shoot the breeze. But let’s face it, you can’t possibly hold a meaningful relationship with 500 people. So what I generally try to do is keep it a step above acquaintance, by making mental notes of what they do and how they could be helped, and making introductions when possible. 

    Of course, it’s easier for me, I probably have < 100 meaningful contacts… I can't even imagine having 1000+ people stumbling over themselves to introduce themselves to me and how I would manage that. There are only so many hours in the day!   

    In general — I believe in karma and giving back though, kind of like RubyRiot here in Boston a few weeks ago. You meet people, they try to help you, you try to help them… it all kind of works out in the end. At least I hope it does! 

  • Anonymous

    So the new 2011 Boilerplate edition is out then?

  • The upswing in requests for networking calls from current and former i-bankers is impressive.  They are certainly an adaptive and reactionary crowd.

  • Anonymous

    I got a great one the other day.  It started:

    Matt –  great to meet you at the JMP Conference
    the other day.  As I mentioned

    Here’s the problem.  I wasn’t at that conference.  My CFO was.

    No return email.

  • i get this a lot for TechStars applicants.  i hate feeling like an ATM.

    blogged about it re: VC’s a while back, too…

  • Are they trying to get all of the quite-hot tech companies to IPO and kill again the web sector?

    • Mo

      Too much liquidity in the financial system. Stock is overvalued. Inflation is coming. They are just looking to saving the assets.

  • During a brief period of time when my prior startup was the featured story in an article in Technology Review, I got flooded with emails and calls from these people. I was too naive to to filter effectively, so I took each request sincerely. This particular activity is the only one I can remember that concluded with ZERO signal to noise ratio. Fortunately, it was a spike that ended quickly. 

    • Mo

      Did you follow up and they hadn’t respond?

  • You are completely justified in being irritated Brad.  There is a clear line between developing relationships and conducting business development. I had a similar experience funding a real estate project through the EB5-VISA program. I acquired sought after contacts and relationships in the industry and suddenly became extremely popular and not for my good looks. Your investment bankers should be thinking about what value-add they can give before sending you spam. 

  • Osman

    Never Eat Alone should be required reading for anyone attending business school, starting a company, or looking to succeed professionally.   It turns the whole idea of “networking” on it’s head.   

    Real networking is contribution (i.e. helping others) and sincere interaction. It’s also a willingness to receive the same.   Everything else is utter bullshit and a waste of everyone’s time. 

    p.s. Brad – It’s been 10+ years since our first pitch (to Softbank).  I no longer need investment capital, but I appreciate more than ever your continued contribution to the success of others (Techstars, Feld Thoughts, etc). 

    • Osman, I’ve not read the book, but couldn’t agree more with your points.  I was just speaking to a class of CU social entrepreneurs about the “soft stuff,” building a network, socializing an idea, negotiating, etc., and I concluded with that point — it’s about putting in more than you take out.  

    • Keith’s book is great, I was fortunate to meet him a few years ago and he is a very genuine person in the way he communicates. Inspiring.

    • Fantastic book.

    • Actually, Brad wrote what I thought to be an interesting review of “Never Eat Alone.”   =>    “How to Win Friends and Influence People” is still the definitive text IMHO =>  

      • osman

        Shelfari is a little creepy.  It makes me feel like a stalker.    

        With that said, I can’t believe he gave four stars to Dan Brown’s The Lost Symbol.   ;p

  • Social climbing is pretty common everywhere. People see people as a means to an end sometimes. The world is big, opportunities and ideas are happening all the time, but people are unique.

  • All real relationships, professional/personal/familial/whatever, are based upon shared experience.  Anything else is forced, contrived, and hollow.

  • Rich

    Do you think people are beginning to view your investing activities as boilerplate?
    If people view what you do as “automated” or “boilerplate” they’ll begin to see *you* as boilerplate. I was telling someone else that automated busines plan submission technology is a terrible idea. It’s like automated resume submission. It’s gives the perception that the person or business is not unique. It also sometimes forces a person to think in a standardized way. Every person or business is different with completely different needs and different attributes.

  • “They don’t require boondoggles or fancy things; they require sincerity and substantive interaction over a long period of time.”


  • Nice post Brad. 

    If I might be so bold to offer an addendum to your closing two sentences. The meaning behind your closing sentences appears to alert entrepreneurs to, if I may call them such, ‘a wolf in sheep’s clothing.’ I think there is also good cause to caution entrepreneur’s to be wary of engaging in such tactics themselves as they are in ramp up mode. The term ‘hustle’ is used quite a bit in the startup world. Clearly, there is a difference between hustling – in the productive, hard work ethic sense – and hustling in the ‘I will use you as nothing more than a tool/mechanism’ sense, which is the basis of your post. Tactics that cheapen the idea of relationship building should be avoided whether they are targeted at entrepreneurs or coming from them. My opinion anyway.  

    Again, great post.

  • Though I have considerable experience in my domain, I can participate less in what happens on this blog because I lack useful insights to share in most cases so I stay silent an act mostly as a consumer. I am an avid consumer of the information and the advice though. Including insights like this post. 

    It sounds like you are seeing a plethora of disingenuous attempts to use you and that does seem wrong. However, it is hard to have a regularly interacting relationship of mutual benefit when one side has little to offer in comparison. Does that rule out contact when appropriate? Another way to say phrase my thoughts: is the issue the usery in the emails and lack of direct engagement/respect or the lack of relationship building? It seems the later might be hard to remedy if someone doesn’t have a lot to offer but the former issue can and certainly should be addressed by anyone reaching out.

    • I’m totally comfortable doing anything for entrepreneurs any time. So –
      entrepreneurs don’t have to develop a relationship with me – I view it as ME
      having to develop a relationship with them (and earn their interest and

      iBankers (and lots of other folks) are in a different category.

  • I have been getting a ton of emails proposing that I “lead generate” by sending out these blind emails. (in a different context).

    I haven’t spent the time to run it down but I must get several variations on the theme each week.  Somebody is paying a ton of commission money to whore out lists, because all the emails are similar (one week free, guaranteed results).

    You can tell its an affiliate marketing scheme of the worst kind.

    I know they’re using old lists because I changed my email address (after 10 years it had been whored out too much) and they all come to the old one.

    I like Reece surmise they must somehow get show lists, and I really should give out separate ones for each show (like I do for websites), but I don’t think they are getting them legitimately anyway.

  • Mary603uk

    My favorite tweet in a long time!

  • Anonymous

    This is too funny, Brad.  Just yesterday I had an entrepreneur (a sincere one) ask for an intro as he saw on LinkedIn that I was connected to you and you were connected to the person he was trying to reach out to.  I explained that I didn’t fell comfortable doing that as you and I had only met once and didn’t have a strong enough relationship (hope we do over time).  I had to chuckle when I read this post a few hours later.

    • Mo

      The difference is that Brad defends his turf, you are not. Investment bankers want to upload excessive cash bypassing VC.

  • Brent

    Brad, what is your experience in cold emailing companies with a legitimate business opportunity? 

    I just finished sending cold emails to about 4 people, BUT here’s the difference.  Whenever I am “cold emailing” someone I sit and read about them, their company, their needs, and try to make sure it is a fit.  I am an inventor and entrepreneur who developed a wearable interface device and the companies I contacted were ones I felt would appreciate the opportunity.  After I am sure it’s a fit, I carefully compose each email and tailor it to the individual I am writing too, spend some time on it.  In my mind, if I am going to cold email at least I am going to put some care into the email.   I think people pick up on that.  So I don’t know if this makes my approach acceptable, but I would never ask for an intro from someone I don’t know really well.  And I only cold email if I have already exhausted every other avenue.

    And so far?  The warm intro I got through an associate has already responded.  The cold emails?  Nothing yet.  But it has worked for me in the past.  I often question if emailing a high level executive results in the email actually reaching them or not.

    I have an entrepreneur friend who cold emailed a number of CEO’s etc. and formed a working business relationship with them through it.  (Of course she had to go see them in person eventually…)

    Thanks for the post Brad, I will start lurking on your blog now. 😀

    PS – I have determined that when I am on the receiving end of an email from a sincere entrepreneur that I will remember what it’s like being in their shoes and try to help them.  I am seeing this attitude in many seasoned entrepreneurs and I LOVE IT!

    • This is a good approach!

      I realize I wasn’t clear enough in my post that I try to answer 100% of the
      emails I get from entrepreneurs. I view it as MY responsibility to build a
      relationship / trust with any entrepreneur who reaches out to me, even if
      it’s to say “thanks for reaching out – this isn’t something I’m interested

      My frustration was with “transaction relationships” (e.g. investment
      bankers) who were trying to pretend to befriend me only to get access to an
      entrepreneur I was working with.

  • Matt M.

    Isn’t it safe to say that the entire investment banking industry needs to evolve? Often 7% to take a company public? Let’s say GroupOn prices at $1B – that is $70MM in banking fees. What risks are these i-banks really taking when these order books are so oversubscribed? How much many did LinkedIn leave on the table? How will much GroupOn leave on the table? Or in return for the 7% are these companies really buying a “buy” rating, easy street numbers to beat for the first few quarters out of the gate, and three banks that will make a market in the the stock?

  • most investment bankers wanted a relationship with me and our portfolio in 1999 and could care less about me and our portfolio by 2001. a few continued to care. they are the ones i go to now. i don’t even reply to emails from the rest of them anymore. they are dead to me.

  • Very interesting article! Love the concept of “transaction relationships.” My co-Founder and I really believe there is limit to how many relationships can come from networking events (or other professional events).   It’s not just about making the connection, but nuturing the relationship and growing it. 

  • Paul Kulas


    When was the last time your company, or any company you’ve been involved with, has invested in someone you had not met, or that had not been referred to you?

    I’m guessing the answer is never? 

    Even the answer is “once or twice”, don’t you think it’s a stretch to say, “We invest in companies”? Shouldn’t the line go, “We invest in people we’ve had experience with, or that one of our trusted associates or go to sources sent us”? Shouldn’t you be upfront with entrepreneurs, let them know that the chances of them contacting you off your website and then getting a deal from you is slim, and none?

    And isn’t this the case with the VC community? Sure it is. Then why do VC’s conduct workshops, have seminars, etc., ask for business plans, when they know there’s very little chance anyone who signs up or who does so, will get anything more than 3 days of hot air, or the standard, “Your business is interesting but we’re not interested”?

    So really what you’re proposing is that I somehow get a connection going with you, then keep the connection for years (like sending strangers xmas cards) for when “I’m going to need you” — for money I guess. That’s so…phony. Then, if that’s all the relationship had, why would you invest in them? So you invest in those who are good at keeping phony relationships going?


    • Actually, many of companies we invest in are founded by people we
      didn’t previously know. Several, such as Brightleaf and Organic Motion
      are people that randomly contacted us as a result of blog posts we
      wrote. And almost all TechStars companies are people we didn’t
      previously know.

  • Anonymous

    Great post. Work, like life, is all about creating lasting relationships. It’s amazing that some people don’t get this.