Note: A version of this post appeared in my semi-regular column on AlleyWatch.
Between applications to Dreamit and the many startups who approach me directly, I speak to a lot of entrepreneurs. And, while I love that part of my job, one of the least pleasant things I have to do as a mentor is tell entrepreneurs when, IMHO, they are wasting their time and need to move on. It’s so unpleasant, that I know many mentors who simply don’t do it. They gently point out “difficulties” but just don’t want to take a chance that they might offend the founder because he might badmouth them so they praise his “hard work” and urge him to keep fighting the good fight.
I don’t do that.
Your time is too precious to waste so if I think you are going down a dead end, I will be bluntly and brutally (albeit politely) honest with you.
Sometimes, that backfires.
The following is an exchange between me and a Dreamit applicant. As background, I had already seen the applicant pitch at other events and knew even before seeing his application that his startup was “not a fit” for Dreamit. His actual application blew past all prior Dreamit records for answer length. I would call his answers “epic novels” except that that implies a logical and narrative structure that was entirely missing. Suffice it to say that, because of this applicant, all Dreamit application questions now have character limits.
It started with this DM:
Why didn’t my company get into Dreamit? I don’t like getting rejecting from accelerators, but they keep telling us to apply again.
Per your dm on Twitter, you asked for some feedback on why [COMPANY] was not selected for Dreamit this cycle.
You are attempting to create a new social network, something that is brutally difficult in the best of circumstances. In the absence of significant traction (>5000 MAU, and rising fast), there is simply no evidence in the market that you are solving a real problem for a meaningful number of people.
I could probably stop there and end with encouragement to apply again when you have made more progress (as you pointed out that most accelerators do) but I won’t.
I’ve seen you working on this concept for a fair amount of time and, while I respect the hustle and hard work, I respectfully suggest that it’s time to move on to the next venture. You have given [COMPANY] enough time and put in more than enough effort that, if this were going to catch fire, it would have already.
You are clearly passionate about this idea and I know it will be hard to move on – I’ve been there myself and know it first hand – but the longer you continue down what is increasingly looking like a dead end, the longer you are putting off the next idea which might actually be the one to go the distance….
Regardless of what you decide, I wish you the best of luck.
Thanks, but I beg to differ and [COMPANY] is much different than any other social network and nobody does things just like [COMPANY]. People may have called Elon Musk crazy to create a new car brand.
Side comment: No one called Elon Musk crazy. By the time he’d started Tesla he’d more than earned his chops. As a general rule, if you are unknown and propose something really out there, you are “crazy” but if you are a hugely successful entrepreneur doing the same thing, you are “bold.”
I believe it’s catching on, and my 13,000 followers on LinkedIn and over 10,000 members is reason to believe. We’re more of a niche network, and there’s no way to move onto something else with all of the effort I put into this. There needs to be a new social networking site as the others do not do a good job. It solves many problems, such as we don’t comment on the photos, less inclined to have bullying. We don’t have people’s information exposed all over search engines like anyone else does. Likewise, our concept brings communities of people together at schools through networks and communities. We have a patent on our tagging and other bigger ideas, so that people can be who they are in photos, which could potentially lead to future job opportunities. We categorize the photos into teams, and we’re building AI technologies to recognize a photo team photo, etc.
I thought we would’ve been great with your partnership with [DREAMIT EDTECH PARTNER].
Many people who join [COMPANY] love my idea! You’re just making up an answer, and I challenge you to find another company you accept in your program that has over 13,000 followers on LinkedIn or has put the amount of effort into a site that I have. We have been challenged to do a lot of great things because we need to raise capital to do them. As someone who worked at Bunk 1, I’m shocked you would say something like this because you know how important camp and team photos are.
Side comment: I’d have responded to him but before I could, he sent me this next email.
Your skepticism makes me want to do a better job, not change everything I’m doing. I hope whoever accepts me and [COMPANY] will make you believe in what I’m doing someday. How many accelerator programs are there? You see my point, yours just so happened to get lucky with a few hits, some of which are in social media such as [Dreamit Alumni]. What if someone were to start another accelerator, would you tell them to do something else? You see where I’m headed, the competition is good and fair. There needs to be a new social network and we’re not the only ones doing this. I wish I had no competition, but the way is now there are many upstarts in the social media space.
Side comment: And before I could respond to this, he sent me yet another email….
This is a quote I think is great and sums up a hard working entrepreneur. I’m in this to win it. I’ll do anything to make [COMPANY] succeed because I know it will and I fight every day to get new people to join [COMPANY]. I can’t wait till the day I win!
“First they ignore you, then they ridicule you, then they fight you, and then you win.” – Mahatma Gandhi
Side comment: Wait, I thought he was Elon Musk. Now he’s Gandhi? But wait, he quickly sent me a 4th email….
Instead of just wishing me luck, can you like my update? I don’t want luck, I want mentorship and growth to my company. That’s why I applied to the Dreamit accelerator. I guess I’ll have to apply again or to another accelerator who will believe in my dream because Dreamit doesn’t believe in the dream as I thought. I’m upset, but if you want to cheer me up, please like my update because I believe in [COMPANY] and what we’re doing. We have a lot of great ideas with [COMPANY] and we’re growing really well!
Please like this update:
With respect [APPLICANT], you missed my point entirely.
I could very easily have simply wished you luck but instead I gave you my candid opinion of [COMPANY]’s odds of success (extremely slim) and frank advice for you.
That is mentorship. It’s just not what you had hoped to hear… but often that’s what a real mentor does.
You are welcome to disagree – I’m sure Mark Zuckerberg had many doubters too – but at some point you have to wonder, “Maybe I’m not Mark Zuckerberg.”
Either way, I wish you the best of luck.
Thanks! Every company you bring on has a slim success rate. What you’re saying isn’t new to me. I know with my work ethic and my idea that I’m bound to succeed. You should only see the billboard I just spent thousands of dollars on….
Side comment: a billboard?!
…I just purchased 50,000 flyers to distribute. We need to grow, and I see [several Dreamit alumni] raising millions after being in Dreamit and think you must be doing something right. Feel my pain, but also realize I work really hard to succeed. I’m inside on a Monday night, turned down a dinner offer to be working and recruiting people to join [COMPANY]. There’s nothing more that an entrepreneur dislikes when you compare them to another entrepreneur. We all know we are not the same people, and you’re not the guy from YCombinator, whatever his name is.
Side comment to Paul Graham: If you want this guy, he’s all yours.
Do you know any current business students at [UNIVERSITY]? I’d love to have a new campus representative there who is serious about promoting [COMPANY]. I’m a big fan of [BUSINESSMAN], and know he has a great shot of being the next President of the United States, but figured if I can hire a student from [UNIVERSITY] maybe there could be a possibility his company would be able to sponsor [COMPANY] and this student would be able to succeed as a representative. You see the type of ideas I think about, great things and helping the students succeed in college and their career! I’d also like to make [COMPANY] into a more educational portal over time whereas students can upload the class notes, videos and more for those who want to use it as this. This is more than just a social media platform in its evolution. I wanted to do a lot of this stuff early on, but it’s a lot of work. I think if we can get the next President of the United States, whether it’s [BUSINESSMAN] or someone else behind [HIS COMPANY], we can do some amazing things.
Can you get your [UNIVERSITY] alumni email to join [COMPANY]? I’d love to have some alumni supporters from this school! I’ve been trying to get [UNIVERSITY] on [COMPANY], as I totally believe he’s one of the greatest alumni from [UNIVERSITY]. He’s the guy I believe in, and the guy who I think can make a difference with technology, since he’s been there. A lot of people thought his ideas were not going to work, turned him down at one point, and he was able to break through the rejection and find investors.
I hope you can find us someone at [UNIVERSITY]! That’s the kind of mentorship I need, the connection to the people who can help [COMPANY] grow.
Side comment: No, not Trump. He was referring to someone else.
I’ve been out of [UNIVERSITY] for many years but you may want to try [OTHER COMPANY]. It’s a startup too that specializes in recruiting campus ambassadors.
We are trying to work with [OTHER COMPANY] again. [COMPANY] was one of their first companies and their site was in its early stages, now it’s improved. Are you an investor in [OTHER COMPANY]? I’m also working with [ANOTHER COMPANY] and a Startup with a bunch of [UNIVERSITY] students called [ORGANIZATION]. Looking into another one called [YET ANOTHER COMPANY] which [INVESTOR] from [FUND] invested in I believe. There are a lot of accelerators. Another one emailed me today called [ACCELERATOR]. I don’t think it’s as good as Dreamit though, or they are ranked lower, right? [ACCELERATOR] is also lower ranked than Dreamit, right?
Side comment: I’m redacting a lot of names here but believe me, they are silently thanking me now.
Not invested in [OTHER COMPANY] but did come across them as an applicant to Dreamit
Know [ACCELERATOR] very well. I mentored with them for several years before heading up Dreamit NY. [HEAD OF ACCELERATOR] is a great guy.
I think Dreamit is better but I may be biased.
Side comment: If you think you are the accelerator / great guy I’m referring to, DM or email me with the company that this is about and I’ll buy you a drink to commiserate.
You’re better, you ranked higher up in the rankings. Dreamit ranked 10 and [ACCELERATOR] ranked ##.
Side comment: While I appreciate a good ass-kissing as much as the next guy, by this point I just want this to end. So I don’t respond… but that doesn’t stop this guy.
A high school student messaged me today to invest in his startup. Maybe I should tell him to apply to Dreamit. You might reject him though because he’s trying to build a social networking app. Did Meerkat apply as a social networking app or did you see them as something else and they pivoted into social networking?
I wasn’t here when Meerkat applied but they were originally Yevvo and then Live On Air before becoming Meerkat so, yes, they went through quite a few pivots before becoming what they are.
Also, I believe that they had proprietary, hard to replicate, technology underpinning their original concept as well.
Translation: “I know Meerkat. Meerkat is a friend of mine. You sir are no Meerkat.” (In case you don’t get the reference)
Some parting thoughts
As you probably imagine, there were a lot of points during the above dialog where I wished I’d simply said, “Competition was extremely fierce this year. Better luck next time!” and been done with it.
But I stuck with it – probably a few emails too long – because I truly felt that this entrepreneur was pouring good time and money after bad, pursuing a venture that had slim enough chance of succeeding even in theory (new social networks make lottery tickets look like good retirement investments) and that, after several years, was absolutely not catching fire. He was emotionally attached to a dead end. As one entrepreneur to another, I felt I owed it to him to help him try to move on.
It’s easy to latch onto to a few glimmers and think you see the light at the end of the tunnel. This entrepreneur really thought at 13,000 LinkedIn followers meant he had traction but we all know that there are some people on social media who will follow a half cooked noodle if it reaches out to them. More generally, anyone can pump money into getting registrations or followers but that’s rarely what really matters. For instance, for a startup like his Monthly Active Users are the metric that matters and, despite his years of effort and money invested, he had fairly few of these.
It’s also tempting to point to all the unique features and patents your startup has none of these mean a damn thing if they don’t fuel usage.
When you’ve poured as much of yourself into a startup for a long time, it’s extremely tempting to write off negative feedback as outliers or as people who “don’t get it.” And yes, there are plenty of those so you do need to stick to your guns for a bit. But when someone who has experience in your field takes time out of his (most likely very) busy day to give you specific and candid feedback when there is nothing in it for him – and especially when there is a fair risk of downside to him from your potentially negative reaction to his feedback! – you need to listen carefully.
And for God’s sake, if someone is telling you that he thinks you need to move on to something else, don’t ask him to put his reputation on the line and introduce you to a lot of people. What’s he going to say to the person you want to meet? “I don’t believe in this startup and I think the founder should kill it but please go ahead and waste your time talking to him”?
So did I learn my lesson? Probably not. When I see an entrepreneur trapped in a doomed startup, I’ll still say something.
But then again, I never claimed to be smart, just experienced. J
Coda: the other company that the applicant mentioned actually did end up applying to Dreamit, was accepted into the program, and is close to closing its round. When asked about this applicant, that founder’s only response was a facial expression best described as “Bruh”