Great Entrepreneurs Are Like Guided Missiles

fortune-logoNote: A version of this post appeared in Fortune magazine’s Entrepreneur Insider network under the headline “The Difference Between a Great Entrepreneur and a Really Bad One”

Great entrepreneurs are like guided missiles. If you point them in the right direction, nothing is going to stop them from hitting the target.

It starts with passion. At Dreamit, we will always back a missionary over a mercenary. Founders who are in it for the economic opportunity will always quit when the going gets tough. An entrepreneur who is driven by the need — not the desire — to change the way the world currently works will stick with it through thick and thin.

Then it takes empathy — not sympathy. The difference between the two is the difference between feeling bad for someone vs. knowing exactly how that person feels. With empathy, a good founder can look at a feature and intuitively know that it solves a user’s problem. An empathic entrepreneur not only knows that something is a problem in his industry, but he can get so far inside the mind of the specific decision-maker that he knows the buyer will look at the service and think, “This is exactly what I’ve been waiting for.”

A great entrepreneur is neither a weathervane nor an anchor. He has well-reasoned but lightly held opinions. There is so much bull**** out there, with so many people pretending to be mentors who have absolutely no business being one. A good entrepreneur almost never adopts advice without reflection. If somebody gives him feedback that is contrary to his current hypotheses, he digs into the reasoning behind that feedback and, if and only if the logic and evidence are good, he changes his hypotheses.

The best entrepreneurs are quick learners and even quicker doers. You often hear them saying things like, “So I taught myself X,” or, “I’ll figure that out.” They love to learn, but they also know when it’s time to tear themselves away from the books and start doing. You never have to tell them to do anything twice, and sometimes not even once. For instance, a potential customer was talking to one startup in the Dreamit program and suggested that the team look into becoming an approved vendor. When they were done, I mentioned to another startup in the room that they might also want to look into it, whereupon that founder turned to me and said, “I’m already halfway through the application.”

Lastly, the best entrepreneurs have failed before. If you find someone who has never failed, odds are they never really pushed their limits.

Bottom line: When you know what to look for, the best entrepreneurs aren’t hard to find.

Wings of Acquire: Using ‘Angel Groups’ to Find Edtech That Actually Helps Students

the74-logoNote: A version of this post appeared in an article in The 74 Million.


When I first met Adam Fried, superintendent of New Jersey’s Harrington Park School District — and newly-named Bergen County superintendent of the year — he told me, “We want to be a part of the conversation that is happening in the edtech space. For years edtech has been built for us rather than with us.”

Then, a few months ago, Stephen Hodas introduced Fried to Dreamit, which helps launch technology firms in education and other industries globally and which I direct.

Hodas, whose many ventures have included running the Office of Innovation for New York City’s public schools, worked with Dreamit when we first ran a program nurturing education technology startups. When I informed him that the company was launching a new edtech initiative in partnership with Penn State and were looking for principals and superintendents who were, no kidding, seriously interested in working with startups, he immediately mentioned Fried.

“Having an engaged, supportive educator can be the critical success factor for an early-stage startup,” Hodas told me. “Teacher feedback is essential to creating relevant and useful products, but if your model involves selling to schools, then principals and superintendents are the ones who launch your business. Only they can greenlight pilots”

This is what Hodas told Fried as well, but the superintendent wasn’t satisfied with merely advising a few entrepreneurs and implementing a pilot or two. He had larger ambitions.

“I’d spent the past two years bringing in entrepreneurs and empowering my staff — basically doing everything possible to create teachers who are fearless about taking chances,” Fried said. “But ultimately, I’m just one district. And then I thought, ‘What if I were twenty schools?’ Then the entrepreneurs would come to us, listen to our problems, and go out and solve them.”

With that idea and twenty like-minded principals, superintendents, and other school leaders, Fried founded the Northern Ignite Cluster. Its near-term goal: meet every two months with four or five pilot-ready startups capable of addressing real needs in their districts.

NIC held its first meeting in April at Dreamit’s New York office. Four startups currently in our accelerator program (i.e., startups whose businesses we’re helping to develop), along with a company that recently completed our program, demoed their apps and services for the educators.

“The ingenuity and creativity of the apps had real potential for future use by school districts,” said Superintendent Richard Kuder of the Wyckoff School District. “It was invigorating to be a part of the early side of the creative process. I am looking forward to the next opportunity.”

Fried is already looking ahead to how groups of educators like NIC can scale to dozens or even hundreds of members, partnering with scores of startups — and how groups that size will determine which ideas are best.

As we brainstormed possible structures and processes, it occurred to me that there was an organizational model surprisingly close to home: angel groups.

Angel group investing has been around for decades, arising from a time when finding individual investors was more challenging for startups, with the result that investors weren’t seeing a sufficient number of proposals to be confident they were investing in the best. Change “investing” to “piloting” and you have the problem Fried wants to solve.

As angel groups grew to dozens and in some cases even hundreds of members, they did in fact attract many more startups — too many, in fact. The groups developed screening mechanisms to weed out entrepreneurs who weren’t quite ready for investment or who were outside of the sectors that most interested the groups’ members. The process often involved a formal application reviewed by a committee of five to ten members. Only startups who making it through this filter were able to present to the group as a whole.

The possible usefulness of this kind of model to a tech enthusiast like Fried was intriguing, so I introduced him to Mindy Posoff, Managing Director at Golden Seeds — an angel group that invests in young companies with diverse management teams.

Posoff saw the potential immediately. “The power of working within a strong angel network allows you the ability to access a wide range of experiences, perspectives, and resources,” she explains. “In talking with Adam, it became apparent that our dynamic screening, due diligence and investment process could be easily adapted and scaled for his needs.”

With an organizational framework in place, Fried is ready to grow his group. “If you are a district, school or thought leader that would like to be apart of the Northern Ignite Cluster please contact me at We are looking forward to the future and what this will do for our children.”

That Entrepreneur Hasn’t Got a Prayer

alleywatch-logoNote: A version of this post appeared in my semi-regular column on AlleyWatch.

It’s a little surprising that entrepreneurs don’t pray more.

The best entrepreneurs are missionaries, not mercenaries. Even if they are not explicitly pursuing a social impact startup, they are driven by the sense that they can, at least in some small way, make the world a better place.

What’s more, so much of the startup journey hinges on fate. Being at the right event, at the right time, to meet the right investor or chancing to catch the attention of an influential journalist or hitting the market at just the moment when it is receptive to your disruptive service… and just before your competitors get there. Even if you do everything right, so much hinges on fate.

Lastly, karma pays a major role. Founders routinely do favors for people they have just met, paying it forward, knowing that sometime, somehow, some of these favors will pay dividends.

Hmm…. Sounds a lot like religion to me, albeit one oddly devoid of prayer.

A few years ago, I resolved to pray daily. I can’t say I’ve quite hit that mark but I succeed more often than not. And while I try to set aside a few minutes for free-form meditation on whatever issues most stress me, I’ve come to see the value of a structured liturgy.

One prayer, known as “The 18”, consists of 19 (Yes, 19. Long story.) short paragraphs, each an acknowledgement of God’s provision of a specific benefit (e.g., wisdom, health, financial success) and an implicit request for the same. It’s far from the most poetic or inspiring prayer. In fact, it’s pretty much a checklist. And therein lies the brilliance.

You achieve what you focus on. If you are looking for biz dev opportunities, you’ll see them everywhere, from sporting events to thanksgiving dinner (e.g., “oh, your cousin works at…”). If you are looking for a tech hire, you’ll find a way to mention it every chance you get (e.g., “So what’s new?” “Actually….”). So if you take a few minutes each morning to run through a structured checklist, you are basically attuning yourself to those opportunities.

It’s not that God is specifically answering those prayers (although who knows?) so much as that the act of praying opens your eyes to what’s already there. It’s as if $20 bills are strewn across the sidewalk and all you need to do is look (up from your smartphone) to see them.

What’s more, focus changes how you perceive events. When your train suddenly goes express and skips your stop, you could get annoyed at the delay. But if your focus is on getting in shape, you’ll enjoy the extra exercise. If an API you rely on is discontinued, you can either rue the setback or welcome the opportunity to see what additional functionality you can access with the newer APIs. It’s all a matter of mindset.

Scott Adams, creator of Dilbert, used to write “I, Scott Adams, am a successful syndicated cartoonist” 15 times each day. Ultimately, (and with the help of George Shultz and Gary Larson’s retirement) he became the #1 cartoonist holding a pen. He credits this affirmation with focusing his mind on the potential opportunities that were out there for the taking.

So what are you going to pray for today?

I Know What Your Biggest Weakness Is. Do you?

alleywatch-logoNote: A version of this post appeared in my semi-regular column on AlleyWatch.

I interview a lot people – applicants to Dreamit’s accelerator program, prospective employees, interns, etc. – and one of the questions I never ask is, “What is your biggest weakness?”

I’ve learned that you never get an honest answer. At best, it’s a test of the candidate’s negotiating skills as they try to figure out what the lowest ‘offer’ they can put on the table is that is just credible enough to keep the bidding going. At worst, it’s just an invitation to lie. But the real reason I never ask this question is, I already know the answer. In fact, your biggest weakness is the same as mine:

Our biggest weakness is the weakness we are not aware of.

We all have parts of our skill sets that are not as strong as others and we all have character traits which, while positive in some situations can be counter-productive in others. But since we know what these are, we generally have ways to compensate for them or even to neutralize them entirely.

If it is a set of skills that were lacking, we choose people with those skills to help round out our team. If it is a critical skill that we think we need to internalize, we take the time to find the resources we need to study up and get up to speed.

If we have a tendency to make quick decisions but are currently facing a complex problem that requires analysis to tease out all the possible repercussions, we put processes in place to make sure that we have examined the problem from every angle. Conversely, if we find that we tend to analyze problems extensively, we learn to recognize when we are in a fast-moving situation and create decision rules that ensure that we know when our analysis is good enough to make a decision so we don’t miss out on opportunities.

But if we are not even aware of the weakness…?

Recently, I screwed up. I was concerned about one of our recent tweets and I posted my feedback to our Slack channel. Read a certain way, it could have been perceived as critical of a colleague’s performance. I frequently discuss with entrepreneurs the importance of proofing emails by putting yourself in the shoes of the recipient to make sure there are no ambiguities or potential tone issues before hitting Send. I also caution all the Dreamit startups I work with that the speed and informality of social media can lead you to share info that you should really think twice about making public (or at the very least, phrase differently for public consumption). But the relative newness of Slack tripped me up. It feels fast and frictionlessness like texting or Twitter but is neither fully private nor fully public. Unlike email, you don’t initiate a post by entering the recipient’s email address or by selecting between Reply & Reply All; the path of least resistance is posting to the entire channel – effectively default Reply All – and you have to actively switch from the original channel to a different channel to direct message someone. In short, it felt familiar but functioned differently. I had a blind spot I didn’t know about… until the crash.

Fortunately, it was only a fender bender. My colleague pointed out what I’d done and I deleted the post. No lasting harm done.

But with the tools we use changing so rapidly, with the competitive landscape we operate in evolving so quickly, you have to wonder what other accidents are just waiting to happen.

So yeah, I already know your biggest weakness. Except that I don’t. And neither do you.

Startup CEOs: You Must Change

fortune-logoNote: A version of this post appeared in Fortune magazine’s Entrepreneur Insider network under the headline “How to Get Your Employees to Stop Wasting Time”

Congratulations. You’ve got some customers, you’ve raised some money, and now you’re ready to expand your business.

Now you’re in trouble.

The problem is that the very skills that got you to this point are largely unsuitable to take you to the next milestone. You need to change. You need to dodge hand grenades rather than jump on them.

The startups at Dreamit are all “A teams.” If there’s a problem, everyone raises their hand. Or as one of my partners likes to say, they see a hand grenade and everyone jumps on it. Sometimes they even wind up fighting over who gets the grenade. And even after they have assigned the problem to one team member, the rest of them will probably still end up walking over to that team member with more suggestions.

This is great when you’re an early-stage startup, but once you’re at 10 people or more, it’s just not workable. That team member will end up wasting more time interfacing with the other team members than actually solving the problem. You, the CEO, need to be able to assign the task to one person and have everyone else get out of his way and do their own work. Divide and conquer.

The change, though, has to begin at the top. Of all the un-scalable resources and all the un-scalable inputs in the world, the least scalable commodity of all is the CEO’s time. That’s why large corporations pay armies of people to guard their bosses’ time as if it were gold in Fort Knox. You’re not there yet, but you have to start thinking that way. Yes, you still need to be accessible. And yes, you still need to have your pulse on everything going on in the organization. But if you try to do everything, or even just the most important things, you won’t get anything done. You need to start dodging those grenades.

Start by drawing up a list of all of the important things that you need to accomplish over the next couple of months. Then, item by item, figure out who within your organization can tackle each task. The key here is not to find the person best suited to solving the problem, but rather to identify everyone capable of addressing it. This gives you the most options when it comes to divvying up your resources. If you find that you systematically are out of resources overall or lack resources to attack certain types of problems, then you know who your next critical hire is. Most importantly, your goal is to get as many of those things off of that list as possible so as to free up your time to focus on what’s going to move your business forward as a whole.

At this point, several of you are probably objecting. You’re probably thinking, “But these are mission critical items. I need to nail them perfectly, not just do them well enough.” Truth be told, the number of situations where that’s true is far fewer than you’d think. It’s more important that you focus your attention on growing your business than on resolving tactical issues, no matter how important that specific client is nor what the impact of a particular technical decision might be.

There’s a story I heard in business school about a professor who shows up to class with a bucket. He starts off by putting some rocks in the bucket, filling it to the top. He then asks his class, “Is this bucket full?” The class answers that it’s full. He then takes a bag of gravel and pours it over the rocks in the bucket. The gravel fills in the spaces between the rocks, and the professor turns to ask the class again, “Is this bucket full?” The class, again, seems pretty certain that the bucket is full. He then pulls out a bag of sand and starts pouring that on top of the rocks and the gravel. The sand filters into the spaces between the gravel and the rocks until it reaches the top of the bucket. The professor asks the class again, “Is this bucket full?” The class isn’t quite sure at this point, but ultimately most of them agree that it’s finally full. Then the professor takes a jug of water and pours it on top of everything in the bucket, and it seeps into the sand and the gravel and the rocks until it reaches the top of the bucket. The professor turns to the class and asks once more, “Now is the bucket full?” The class is, at this point, too uncertain to even answer, so the professor smiles and says, “Don’t worry, it really is full now. What does it teach you?”

The students decide it means that no matter how busy you think you are, if you’re smart about your time, you can always fit in a few more things. The professor looks at them sadly and says, “You missed the point entirely. If I’d started with the sand and the water, would I have been able to get the rocks into the bucket?”

The rocks are the big strategic initiatives that move your business to the next level. When your startup is very early stage, the rocks are obvious. In fact, pretty much everything is a rock at that point. But as you grow your business to the next stage, more and more of what you deal with are actually just pebbles and sand. That’s why you build your team up—to take small things off of your plate so you can focus on getting the rocks into your bucket.

No matter how hard you try, though, you will still be so busy that you won’t know what to do with yourself. The difference is that now you’ll be focusing on the things that actually matter.

Your Great New Idea… That Everyone Else Also Just Thought Of

fortune-logoNote: A version of this post appeared in Fortune magazine’s Entrepreneur Insider network under the headline “Here’s How to Know Your Business Is Headed for Disaster”

Something that never ceases to amaze me is how an idea will arise and suddenly come at me from several directions at once. Other entrepreneurs all swear to have come up with that same idea independently, and I believe them—it’s happened to me more than once.

To be clear, I’m not talking about x-for-y variations (e.g., Airbnb for cats or Uber for bicycles). I’m talking about genuinely new ideas. My theory is that startup concepts each rest on a set of memes and technical capabilities. When all of the relevant building blocks are in place, conditions are ripe for that startup concept to be discovered. And with enough really smart entrepreneurs actively and constantly alert for new opportunities, it’s only natural that several of them will come up with the idea simultaneously and independently.

That said, there are some startup concepts that are truly out of left field—that leapfrog a lot of these building blocks. So how do you know if you have a really revolutionary breakthrough or a more garden-variety disruption?

You start by searching. Before you build—before you even model your business in Excel—spend some time Googling up any possible description of the idea you have in mind. In many cases, you’ll find that four or five companies on the first results page are already doing it, and you can simply move on to the next idea.

If you don’t find anything, try searching using keywords that describe the problem you’re solving as opposed to keywords describing the solution you’re proposing. You may find direct competitors that way. At the very least, you’ll better understand how your prospective customers currently relieve the pain point, and you can assess whether you’re a quantum level better or simply an incremental improvement. (Hint: It’s really hard to get attention, much less change user behavior without a clear, compelling, and overwhelming benefit.)

If the field still looks open, go to AngelList and read the short description of every startup in the same sector or sectors that you cover. Yes, read every single one. Every. Single. One.

If you still think you have something new and awesome, go out there and talk to as many smart people as you can, especially if they’re investors or customers on the space.

Don’t worry about them stealing your idea. Most of the people you speak to will never quit their day job, and about 1% will be entrepreneurs with their own ideas. They aren’t going to suddenly look at their startup and think, “My baby isn’t so cute after all. Let’s go steal his baby.” Perhaps one in 1,000 will be entrepreneurs with the right skills, connections, and availability to run with your idea, and it will be immediately obviously who they are. Don’t sweat it.

Instead of worrying about people stealing your idea, ask them to break it. Ask them to tear it apart and show you all of the ways it can fail. And if they can break your idea—and you can’t fix it—thank them. They’ve just saved you years of your life and a lot of money chasing a doomed venture.

If after all this you find that you have something genuinely new, compelling, and unbroken, let me tell you about Dreamit‘s accelerator program.

The Secret to Putting on an Awesome Panel

alleywatch-logoNote: A version of this post appeared in my semi-regular column on AlleyWatch.

Since joining Dreamit, I’ve been on dozens of panels and moderated more than a few of them. Some have been awesome, others have been…less awesome. Want to make sure your panel rocks? Keep reading.

(I’m going to assume you have lined up great panelists. If not, don’t even bother putting on a panel format event. Ok, enough with the blindingly obvious advice and on to the good stuff.)

What separates a great panel from a mediocre one is time management. Take a typical one hour panel with three panelists. After you allow time for the panelists to introduce themselves and for the moderator to set up the questions, each panelist has roughly 15 minutes of actual talk time. So how do you make the most of that limited resource?

  1. Pick your questions wisely.
    If you know the topic reasonably well – and if you don’t you have no business moderating the panel – you should be able to brainstorm an initial list of questions. Share it with the panelists, other experts, and perhaps even some members of the target audience to get their feedback on what would be the most interesting questions to ask. Ask them to suggest questions you haven’t thought of.
  2. Know who to ask which question.
    If you ask a panelist a question, he will most likely answer it even if only to restate what another panelist just said or to add a minor nuance. That’s a waste of time that could be better used on a new topic. So just ask one panelist and then move on to the next question. You don’t need all three panelists to answer every question.
  3. Get the panelists thinking about the answer in advance
    You know what the best part of having a panelist give a long-winded, rambling answer is? Nothing. It bores the audience and sucks time away from more interesting content. But if the panelist hasn’t thought through how he or she plans to respond, your odds of getting a crisp, concise answer go way down.

So how do you pull this off? I’m glad you asked…

Two weeks prior to the panel:
Email the other panelists to introduce yourself (if you don’t already know them) and send them a preliminary list of the questions. Ask them to comment on which questions they think would be most interesting and to add any questions that they think would be worth discussing. Set an explicit deadline on when you would like them to respond. Reading a lists of twenty or so questions, commenting, and adding a few of their own questions is not a big ask so 2-3 days turnaround is not unreasonable.

One week prior to the panel:
Once you have selected the 8-10 questions you would like to ask, send out a poll (e.g., in MailChimp) to the panelists. For each question, ask them to rate (e.g., scale of 1-5) how interested they are in answering that particular question. Include a comments field where you ask them to briefly write out their  thoughts on that topic.

This data should give you an idea of who has interesting things to say about each question. Where more than one panelist is interested in answering the question but where they essentially agree on what they want to cover, simply pick one. If they disagree (in an interesting way, of course), you can pose the question to the second panelist for a counterpoint.

Try to allocate each panelists’ “air time” roughly equally, taking into account their preferences as to which questions they are most interested in discussing.

The added benefit of having them write out how they might answer the question is it that it gets them thinking about how they would phrase their responses. This should increase the odds that they give nice, crisp responses when they are on stage.

The day before the panel:
Circulate the questions that you have selected along with who you ask to answer each one. If they know what to expect and are confident that they will get their chance to answer a fair number of questions that are important to them, they should be able to resist the urge to chime in on the topics that you have assigned to other panelists.

At the panel:
Be awesome.

Good luck and have fun!


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