7 Reasons Why the Book of Esther Is Like a Startup

Here’s a quickie, partly (but only partly!) in jest:

With the Jewish holiday of Purim right around the corner, it occurs to me that the central text of this holiday, the Book of Esther , has a lot to do just about the typical startup journey:

1. A startup that is seemingly an overnight success usually takes 9+ years to come to fruition (“In the 3rd year of his reign… On the 13 th day of the 12th month…”)
2. The best startups attack truly huge markets (“… who ruled from India to Ethiopia, 127 nations”)
3. There is typically an established incumbent that has become complacent and less responsive to their clients’ needs (“But Queen Vashti refused to appear by the king’s order…”)
4. Many startups operate in stealth mode for an extended period of time (“Esther did not divulge her race or ancestry, for Mordechai had instructed her not to tell”)
5. Even after landing their first big account and getting a substantial lead, steps often still face stiff, well funded competition (“After these events, King Achashverosh promoted Haman… above all his fellow ministers. ‘…and I [Haman] will pay 10,000 silver talents to… the King’s treasuries.’ “)
6. But great startups know how to mobilize their entire community to counter any threat (“Go and gather all the Jews who are in Shushan and fast for my sake, do not eat and do not drink for 3 days, night and day.”)
7. And when the startup finally best all the competition, they jacked prices up through the roof! (“King Achashverosh levied a tax upon the mainland and the islands of the sea.”)

Cutting Through The Tech Startup Clutter (interview by Titania Jordan)

I was interviewed by Titania Jordan for the 3Ci CONNECT Show while at Shadow Venture’s annual Summit in Atlanta on the genesis of Dreamit UrbanTech and what we see coming down the innovation pike in PropTech and ConstructionTech.

Why I Hate Your Market Size Slide

A version of this article was previously published on Propmodo in Sept 2018

Given how much topic annoys me, it’s surprising that I haven’t written about it before.

As managing director of Dreamit UrbanTech, I see well over a thousand (if not 2000) pitch decks a year. Now that we work with more mature, pre-Series A round startups, most of our applicants have already raised a seed round and may have even gone through other accelerators, so it’s more than a little bit surprising to me that somewhere between 10-20% of those applicants still have unnecessarily complicated Market Size slides.

Here’s an example of what I mean:

Yeah, you’ve seen it before too. Looks kind of impressive, doesn’t it?

Unfortunately, here’s what I see:

Let me break this down for you you:

• Total US Construction – The startup sells software. Why do I care about money spent on concrete, labor, etc.? That’s no more relevant to this startup than Dim Sum sales in Moscow.
• Contractor Software Spend – They sell software to subcontractors. If a general contractor is spending $50K or $100K a year on Procore, why does that matter? Those GCs have no use for this startup’s product, will never use it, and will certainly not be spending any of their money on it. Might as well toss in revenue from video game sales for all that has to do with this market.
• Subcontractor Software Spend – Right type of product, right customers – now we’re getting somewhere. Probably still a top-down estimate but at least this is less obviously wrong.

Top down is for convertibles, not pitch decks

Let me let let you in on a secret: top-down market size estimates are almost always incorrect and generally useless to an investor.

Why are they almost always incorrect? Because they typically capture a lot of related spending on different types of tools. In the example above, the figure includes spending on other construction related software, not to mention more general purpose software like Microsoft Office and Quickbooks. Furthermore, the top-down approach ignores pricing. Let’s say, hypothetically, that you make software that replaces absolutely everything the subcontractor might possibly buy but do it at a tenth of the price. By definition, your market is 90% smaller than the top down estimate suggests. Alternatively, say you provide a solution that’s much more functional and valuable than anything on the market and expect to price at a premium to existing software. In that case, the top down market size estimate understates your potential.

The more accurate and useful way to estimate your market is bottoms-up. It’s really not that complicated. At the end of the day, it is simple third-grade math: Total number of potential customers times what you plan to charge. Really, it’s that simple.

So that’s what an appendix is for…

I called top-down estimates “generally useless” instead of simply “useless” for a reason. They occasionally are a useful appendix slide as a sanity check. If you are creating a completely new product category and your bottoms-up market size estimates are large, it’s good to know the size of the total budget you are competing for. For instance, if your bottoms-up estimate comes to $100B and the software spend for the entire construction industry is $130B, you are essentially arguing that your customers will either stop buying 77% of all the software they currently use to buy yours or that they will manage to steal budget from other departments. Not entirely impossible, but extraordinary claims require extraordinary proofs. Needless to say, you’ll get a lot less pushback if your bottoms-up estimate came to ‘just’ $10B out of $130B.

Who’s on first?

As simple as the above TAM equation is, it still has two variables: number of customers and price. So if you haven’t told me what you charge, the equation isn’t going to make much sense. You need to define the price variable before adding the number of customers into the mix. That’s why your Revenue Model slide should almost always immediately precede the Market Size slide.

In some cases your Revenue Model may be a bit complicated. Your price may increase based on usage (e.g., number of seats or concurrent users), frequency (e.g., API calls, reports or searches per month), or value received (e.g., which modules they subscribe to). Your Revenue Model slide should include this detail at a high level but should also clearly show what you believe the average spend will be across all your customers. Assuming the reader thinks that estimate is plausible, he or she can seamlessly plug it into the market size equation on the next slide.

Maybe we can meet in the middle?

Typically, when you see the infamous 3 circles the only number that matters is the bottom circle but, alas, not always. Sometimes the Total Addressable Market is actually the middle circle. For example:

Now we have to actually think about it (dammit!). If the startup is pitching software for roofing subcontractors, the bottom circle is the relevant one (and I can stop reading right there because that market size is way way way too small). But if a founder is making software for all subcontractors and they’ve identified roofing subs as the first subsegment they are targeting as they go-to-market, then the middle circle is the one that matters when it comes to TAM.

Bear in mind that the bottom circle is not wrong. It’s even interesting and relevant information as far as an investor is concerned. It is simply in the wrong place. “TAM” means “Total Addressable Market”: if everybody who could use your software uses it, how big is the market? If you choose to sell to some types of customers before others, that information belongs on your Go To Market slide.

Don’t sell yourself short

What would you make of this slide?

At first glance, this looks like a $200M market. That’s a nice size for a self-funded company, but it is generally not considered large enough for venture funding. But take a look at footnote 3. This company is assuming that they ultimately get only 25% of the total market. This may very well be true but they are selling themselves short. Investors think in terms of total market size; all our rules of thumb implicitly assume that the startup will only capture some of that total. In theory, we should be able to correct for that but, psychologically speaking, the low number sticks in our mind. Plus that assumes we caught this in the first place. As I mentioned before, we don’t particularly like it when you make us think.

When top-down and bottom up are the same

Before I get more than the normal volume of hate mail and ‘gotcha’ email, there is one legit exception to this rule. Under certain revenue models, the top-down estimate is actually what drives your bottom up number. For instance, if this software was used for purchasing construction material and had a revenue model where the software was free but they got a commission on all sales of, for instance, 4% of contract value then the top down figure of everything spent on construction supplies is actually the entirely relevant input to the “third-grade math” equation for market size: Total purchases x 4% = TAM.

You would still have to be very careful to exclude the types of construction supplies that are not on their platform (e.g., if you can’t sell cement, you have to pull that spend out) but in this case, the top-down data is not only valid but necessary.

“The TAM Commandments”

With the above in mind (and apologies for the awful pun), here’s a quick recap of what you can do to make your Market Size slide as effective as possible:

• Thy TAM shall be a single figure.
• Thou shalt have no other market figures before (or after) the TAM and expect Me to figure out which one (or two) to ignore.
• Thou shalt use bottoms-up estimates. Top-down estimates are an abomination. (Except when they aren’t)
• Remember thy Revenue Model slide and keep it before your Market Size slide
• Honor thy Go To Market with its own slide. Leave GTM strategy off the Market Size slide.
• Thou shalt not kill your Market Size by reducing by your expected market penetration
• Thou shalt email me if you can figure out a way to riff on adultery, theft, bearing false witness, and/or coveting your neighbor’s wife in this context.

Thanks for reading and please share this with all your friends… because I’m sick and tired of bad Market Size slides.

Note: This example is loosely based on Dreamit UrbanTech alumni Knowify. Their Market Size slide looked nothing like this and, for those of you who actually read the footnotes on the charts, the $800M TAM is 800K subcontractors in the US x an average software subscription price of $1000 per sub. So in other words, Knowify did it right. 🙂

PropTech Pitches That Are Past Their Expiration Date

A version of this article was previously
published on CREtech in Sept 2018

Coming off another successful recruiting for our 3rd Dreamit UrbanTech cohort, we had the pleasure to meet quite a few truly incredible startups.

This piece is not about those startups.

This is about the other ones, the startups that, like milk past its expiration date in a coworking space refrigerator, we’d really like to quietly disappear and be replaced with something fresher. So, after canvassing a few of my colleagues, I’ve compiled this list of startup pitches that, absent extenuating circumstances, we’d just as soon not see again.

It’s a community portal for tenants

I live in Manhattan. I don’t even want to talk to my neighbors in the elevator so why would I want this? In virtually all the buildings I’ve lived in, there has invariably been “that guy” (or woman) who has tried to rally the other tenants to be more social. Often, we like “that guy” a lot – he’s nice, he takes our mail in, signs for our packages, etc. We just have no interest in what he’s trying to do.

Kidding aside, there’s nothing about this idea that couldn’t have been done as far back as the late 90s which should be a huge red flag to any entrepreneur considering a startup like this. With so many hungry and talented entrepreneurs out there, good ideas don’t just sit around waiting. In fact, established companies like BuildingLink have community sections that are invariably ghost towns. If you have a burning conviction that the world needs a tenant community portal, you should consider the possibility that you are “that guy.”

It’s a real estate crowdfunding site… but with blockchain!

The most charitable thing I can say about these pitches is that they (or most of them, at least) were not ICOs.

We started seeing pitches for real estate crowdfunding sites as far back as 2014, if not earlier, and there are already a number of players in the space with significant head starts (RealtyShares, Fundrise, RealtyMogul, Patch of Land, etc.) so if you are a pre Series A startup in the space, you are pretty late to this party. Since these are basically marketplace plays, first-mover matters.

But wait!” you say, “we use blockchain!

So what? It’s not that hard to keep track of fractional shares in a building using an old-school, centralized ledger. If you standardize the legal documents and purchase process, you’ve already removed the friction on this process. The hard part here isn’t transactional friction but marketplace liquidity: you need enough buyers on the platform so that when someone wants to sell their shares (or tokens) in a property, there is someone willing to buy it. If you don’t have a deep pool of potential buyers, you end up with an asset like small cap stocks: easy enough to buy but hard to sell (especially in a down market!)

The possible exception to this rule are companies like Harbour who focus on tokenizing high-end trophy properties. These are the blue-chip stocks of the real estate world. There will likely always be smaller investors willing to own a piece of the Empire State Building. So giving its owner the ability to sell part of it to a mass market rather than to the current small circle of big players who can afford to invest at that scale both greatly increases marketplace liquidity and reduces transactional friction, unlocking (at least in theory) significant value for the building owner.

It’s a lead gen site for commercial real estate

I have the utmost respect for lead gen and, given the size of these transactions, there is potentially a lot of money to be made selling leads to landlords and their brokers. The trick is getting the tenant to start their search on your site… and you need to do it in a way that your competitors cannot immediately copy or else your cost of customer acquisition will be bid up until your margin is gone. Put another way, if you are using Google AdWords to drive traffic to your site, so can your competitors.

Zillow, for instance, succeeded in creating a site that residential buyers know to go to at the very startup of their home or apartment search by aggregating and cleaning up messy, fragmented public data and presenting it to the public in an easy to use interface. In theory, anyone could have done this but they moved first and fast, creating brand equity that’s hard for a potential competitor to displace without either creating something a quantum level better or spending a lot of money on advertising to launch a competing brand.

Our app helps community residents get in touch with their representative and get more active in local politics

If they wanted to do that, wouldn’t they start by at least voting? This is an example of civic tech backwards think: instead of creating an app to fill demand, they want to create demand with their app. And since here too, people have been banging their heads against this wall for nearly two decades, if you still think the public is just dying for an app like this, it’s very possible that you are “that (other) guy.”

We are a chatbot for residential brokers

It is telling that these startups rarely include successful real estate agents on the founding team. Converting a productive buyer into a client is mission critical, especially in an industry with little competitive differentiation. Agents convert products with personalized service and emotional rapport. A chatbot is the exact opposite of this and, as a result, agents are extremely reluctant to rely on them for this stage in the conversion funnel.

The rental side of real estate, especially on the lower end of the market, can be a brutal, time-consuming slog. Most agents transition from representing renters to other parts of the market as soon as they possibly can, leaving this segment to newbie agents or high volume / low service shops so it’s conceivable that a chatbot for renters’ agents might have legs….

We make 3D models from 2D floor plans

There’s value here if you can pull it off but there’s just not enough data in a 2D model to get to something buyer-ready automatically. So either the landlord has to customize the raw results a lot (too much effort for them) or the startup does a lot of post production (and becomes a service industry selling man hours rather than a scalable tech startup).

(Dis)Honorable mentions:

While not full-fledged startups, these phrases were often enough to make us gag all by themselves

Blah blah blah… drones!

Yes, drones are pretty cool and they do have the potential to change a lot of things, both in construction and real estate and the world in general. But if your startup is basically a glorified drone piloting service, you are selling man hours (not a model that VCs like to back), have no competitive advantage and no barrier to entry. To us, you are basically a taxicab company.

Blah blah blah… AI

So what exactly makes it AI (or Machine Learning for that matter) as opposed, for instance, to a simple database query? As the famous quote goes, “I do not think that word means what you think it means.“

… and the user gets a dashboard…

My car has one dashboard. Why would you expect a property manager to want 6 or 7? I’ve head the phrase “dashboard fatigue” a lot lately…

Instead of covering them another dashboard, integrate with their existing dashboard or, better yet, automate the responses to the data you collect so they don’t have to check a dashboard at all… or even think about it. Just. Make. It. Happen.

We’re Houzz meets Uber meets Robinhood

WTF?

Here’s a hint: the Hollywood style analogy should get you an instant “Ah, I get it.” If the investor has to think about it to understand what you mean, it’s a #fail. I don’t care how cool you think it sounds, skip it and cut to simple description.

 

Acknowledgments: I’d like to thank Aaron Block, John Gilbert, May Samali… and all my other less brave colleagues who opted to contribute to this piece anonymously 🙂

What Exactly Is PropTech?

Note: With the increasing interest in PropTech, Bisnow interviewed a number of experts in the field to answer the question “What Exactly Is PropTech?” As the MD of Dreamit UrbanTech, I was one of the people they interviewed. The interviews were published in Forbes under the headline “The Beginner’s Guide To Commercial Real Estate Tech: What Exactly Is PropTech?”

It is difficult to pinpoint when the term PropTech, which stands for property technology, rose to prominence in U.S. commercial real estate.

With the increased use of the term, the challenge is determining what it actually means. Is it synonymous with CRE Tech, which refers to all tech solutions in the entire CRE landscape? Or does PropTech refer to technology that supports real properties — both residential and commercial?

Bisnow reached out to major players in the commercial property tech space to get the scoop.

 

Name: Michael Beckerman
Company: CRE.Tech, RE Tech, The News Funnel
Title: Founder and CEO

“I’m a little biased because my site is CRE.Tech, so I don’t use PropTech. I feel like it’s a term more common in Europe. Everyone I know in my community uses CRE Tech because PropTech, I don’t know that people really understand what that means. It is kind of confusing — does it refer to residential or commercial real estate, or both? Is it only properties? Whereas with CRE Tech you’re talking about finance tech, appraisals, data, etc. … In Europe PropTech is the word they use commonly, whereas here we use CRE tech more frequently. I think [CRE Tech] is more universal, more on brand and more all-encompassing. CRE Tech is the entire ecosystem, whereas PropTech refers to one subset of the ecosystem — I think it is more property-specific.”

 

Name: Mike Sroka
Company: Dealpath
Title: CEO

“We’ve observed PropTech being used synonymously with CRE Tech over the past few years and with increasing frequency over the past 12 months, particularly in the EU markets. The general assumption is that the term relates to any technology supporting real property (residential and/or commercial). This seems quite broad and we’re not surprised to hear that people are finding it confusing. In our opinion, commercial real estate and residential real estate have many differences, are worked on by different people, with different challenges, and require different solutions.”

 

Name: Nathan Dever
Company: Ten-X
Title: Commercial Real Estate Technology, Strategy & Marketing

“The makings of PropTech began in the mid-1980s, marked by the founding of companies that provided software for the commercial real estate industry. Autodesk and NCREIF in 1982, Yardi in 1984 and CoStar in 1987. However, PropTech didn’t really spring to life in a big way until the mid-2000s, when cloud computing, broadband connectivity and mobile devices enabled residential PropTech giants RightMove, Trulia and Zillow to launch and show investors the value of disrupting real estate through technology. Since the mid-2000s, more and more PropTech startups have been bringing new technologies to market that address a wide variety of inefficiencies, scoring more attention and capital from technology VCs and growth funds, which legitimizes the real estate technology movement.

The taxonomy of real estate technology is still maturing. In recent years, it appears the rapid rise of smart real estate technologies, such as IoT (networked sensors, devices), is shifting the association of PropTech to property management technologies, while real estate information technologies and transaction technologies go without their own defining cliché buzzwords. Of course, there also remains much blurriness around the precise definitions of RETech, CRE Tech and FinTech.

To be honest, I try to not organize my understanding of real estate technologies around buzzwords, since many incumbent and insurgent companies have/bring crossover services that fit many of the loose definitions of popular jargon.”

 

Name: Nick Romito
Company: VTS
Title: CEO and co-founder

“In thinking about PropTech today, I’m more interested in talking about it functionally than theoretically. You search Google, you’ll find 10 definitions of PropTech — half focus on the nature of the solutions, but use different words, and half just define the industry as being a collection of companies. For me, functionally there are really two big segments that investors are behind currently. There’s a slice that’s devoted to virtual reality applications. We’re leading the other, larger segment that has a pressing need for solutions today — the transactional, deal-flow side.

The idea of PropTech, for me, is about transforming the commercial real estate industry without disrupting it — integrating cutting-edge technology with big data and predictive analytics that align exactly with what professionals actually do in a way that is much more intuitive, insightful and easy-to-use. No one needs to master a whole new set of processes for accomplishing key goals — the platform will let them do the jobs they’re doing better, on a tremendous scale.

Let me give an example, because any PropTech solution is only relevant to the extent that it addresses the critical pain points faced by real-world industry professionals. Commercial landlords constantly have to track at least two streams of data: first, information about all of the tenants currently residing in all of the landlord’s units across however many buildings; and second, the financial value of a portfolio of owned real estate assets. A great PropTech use case is uniting those workflows, especially since they ultimately need to be anyway. The value of the building depends somewhat on the characteristics of the tenancy, as well as what the leasing pipeline looks like. A smart, easy, intuitive and centralized dashboard that lays out all the data and also makes those vital connections and offers some predictions, assuming it’s built well, is a huge advantage for a commercial landlord.”

 

Name: Zachary Aarons
Company: MetaProp NYC
Title: Co-founder

“In mid-2016, real estate technology surged from being primarily U.S.-based to clearly a global trend. As the global nexus of real estate and technology, MetaProp NYC saw this growth early and led the semantic switch from RETech to PropTech at that time. The term was already used periodically in Europe, but not widely in the United States. Having originally branded RETech as the common term for the entire real estate value chain (anointing 21st Street in Manhattan’s Flatiron ‘RETech Row’ for the cluster of real estate technology firms, including MetaProp, located there), we decided to recognize the term property that prevails outside the U.S. by re-branding the worldwide movement as PropTech. In fact, we now refer to our street as PropTech Place!”

 

Name: Andrew Ackerman
Company: Dreamit UrbanTech
Title: Managing Director

“PropTech is the same as Real Estate Tech. From what I understand, PropTech is the more common phrasing used in Europe and Real Estate Tech more common in the U.S. In deceptively simple terms, PropTech is technological solutions that solve problems for the real estate industry. Let’s break that down:

• Technological solutions — websites, apps, devices, physical materials or any combination of these elements. Not just services, consultancies or brokers (although they might be customers for PropTech startups) and not the actual property development.
• Solve problems — It’s shocking how many startups do things because it is possible or cool without thinking through who actually cares enough to pay for what they’ve built.
• For — As in, specifically for. The real estate industry buys laptops (and phones, toilet paper, etc.) just like every other sector, but just because they are one of your customers, does not make you ‘PropTech.’
• Real Estate Industry — Developers, architects, engineers, construction firms, subcontractors, property managers, landlords, brokers or residents (e.g., tenants, homeowners).

There’s some debate about the last point. Some people carve out ConstructionTech as a separate sector targeting the pain points of architects, engineers, construction firms and subcontractors, but I see enough overlap where startups service both those groups and others within the real estate industry that it makes more sense to me to view ConstructionTech as a sub-sector within PropTech.”

Edit: Since this article was written in Nov 2017, I’ve come around to seeing ConstructionTech more as a separate sector. There are certainly a lot of overlap around the built environment and sensors but I take a very customer centric approach and I am seeing enough innovation that I’d only present to general contractors or subcontractors (but not to developers, for instance) that it deserves to be a separate, albeit related, sector.

 

Name: Charles Clinton
Company: EquityMultiple
Title: CEO

“Much like the term fintech captures the new wave of finance companies that utilize technology to power their business, PropTech captures the intersection of real estate and technology. This encompasses a range of businesses that are as diverse as the real estate industry itself, from leasing and property management to co-working to investing — anywhere that technology is innovating how property is occupied, managed and transacted … While the term has been used within the industry for years, it really exploded in popularity over the last year. Empirical data backs this up. Looking at Google search data as a proxy, it really started taking hold about a year ago and peaked just last month in October 2017.”

Stale Words and Hackneyed Ideas That Make Edtech Investors Cringe

Note: A version of this post previously appeared on EdSurge. 

 

If you go to startup pitch events, you’ve seen it happen:

An entrepreneur says something—something so naïve, egregious and hackneyed—that it makes the investors, along with educators who are now increasingly in the audience, physically cringe. As funders wince and squirm uncomfortably, some are thinking along the lines of: “How do I respond to this pitch genuinely without coming off like a jerk?”

In the interest of fixing this problem at the source, I reached out to some of the advisors and investors in the Dreamit Edtech network to get their “lemon lists” of concepts, statements, and business models that Edtech entrepreneurs may want to think twice—or thrice—about.

For convenience, I’ve aggregated their suggestions into two broad categories: Cringe-worthy Concepts and Modest Missteps.

Cringe-Worthy Concepts

These are not inherently “bad ideas” per se. It’s just that the investor community have seen tons of these, and in order to impress you need to jump right to what makes your approach a quantum level better than everything else out there. Hint: “It’s mobile,” “We have a better UI,” and “It’s for millennials” are not the answers.

Student engagement and retention mobile apps

Yes, this is a big problem. But there are many startups in this space. Most of them offer some variation of the thesis that improving how “engaged” students are in their coursework and community will boost academic outcomes which will then increase retention. Yet academics are not the main reason student drop out; according to a study from Inside Track, it’s the fifth most important factor.

The other solutions I see in this space tend to throw a lot of features (such as calendars, student to student messaging, event check-in, and newsfeeds) into an app and hope better retention just happens. I’d cite a few examples of this approach but, as you can imagine, startups who take this approach rarely get off the ground and those who do don’t last long.

Parent communications platforms

There are already several well-capitalized startups (including Bloomz, ClassDojo, Remind), established companies (SchoolMessenger), and other deep pocket players from learning management system providers that already boast significant traction here. Like Peter Thiel says, if you are not delivering a 10x improvement, you don’t stand a chance.

Chatbots

Chatbots are hip and cool these days and, while I agree that they have a lot of potential, most of the pitches are simply applications that turn IBM Watson’s natural language processing technology loose on a university’s existing FAQ page. If that’s all you’ve got, what makes your business better and defensible? In these situations startups that master the space early get a rush of initial business—until the mass of fast-followers come in and drive prices down to the bare bones.

College recruiting and lead generation

The growing population of 18- to 24-year-olds in the U.S., along with the stream of foreign applicants to U.S. universities (which, to note, has taken a small dip under the Trump administration), the widespread adoption of online applications, and nearly 700 colleges accepting a common application, combine to make college admissions more competitive than ever. So finding and getting into the right college is clearly a major pain point.

The catch is that the vast majority of people suffer it only once. This means that customer acquisition is challenging and your company’s revenue model has to be rich enough to support it. Unfortunately, the days when you could sell a lead to the university solely because a student visited its page on your website and clicked “save” are long gone. For your lead to be worth much to the college you need to have robust data about that student’s underlying needs and preferences, and demonstrate that students value your site or app as a highly trusted source of information and advice.

Peer-to-peer or crowdsourced tutoring network

Simply saying “We’re the Uber of education!” doesn’t make it so. There’s a graveyard full of these startups (such as Tutorspree) and only a few survivors like Wyzant. They almost all underestimate the cost of customer acquisition and overestimate how much usage and viral boost they will get.

To be clear, it is not any specific dollar amount that concerns us; it’s the ratio of customer acquisition cost (CAC) to the lifetime value (LTV) of the customer. As a general rule, LTV has to be 3x higher than CAC for the business model to work. But when I see these kinds of businesses, if they estimate CAC at all, it’s based on a small experiment that won’t scale. So I ask them, “If the economics are that good, have you maxed out all your credits cards to pour every last cent into this customer acquisition channel?”

Invariably, they start backtracking, hemming and hawing, and eventually admit that there either are channels that cannot absorb more marketing spend (e.g., they were bidding on rare search terms that just don’t come up that often) or that CAC starts to rise as others spend more (e.g., startup bidding on more competitive search terms).

Particularly unconvincing: telling us you got a few hundred signups at your college “with zero marketing spend.” What this tells us is that you have no idea what it will cost to get students onboard at the other 4000-plus colleges you do not attend.

Any B2C app for language learning

Personally, I like using Duolingo, and Voxy is a great option for people who want to learn English. But as with tutoring networks, the customer acquisition costs are much, much higher than you think, especially the ones that, like Google Adwords, can scale with you are you grow.

Some of the apps do reasonably well at getting free users, but usage drops off pretty sharply when they are asked to pay anything. That means the acquisition cost per paying customer is very hard to recoup.

Graveyard Ideas

These next few ideas were great…back in the day. Now, the market is pretty much locked up. Startups that are attempting to build the following tools are at least 10 years too late to the party, especially if they’re attempting to tackle the US market.

Yet another student book exchange

How are you better than Chegg (or Amazon for that matter)?

Yet another LMS

Switching something as deeply entrenched in a school’s operations as their LMS is so painful that it’s basically a non-starter. Switching costs are high, and most schools are not likely to switch from solutions like Blackboard or Canvas for the sake of a prettier interface or more “social” features. Sometimes you could give your solution away for free and they still wouldn’t switch. In fact, a freebie option is emerging as some schools are adopting Google Classroom as a lightweight LMS.

Yet another Test Prep Provider

Kaplan, Princeton Review, Tutor.com … the list goes on and on.

MOOCs or General Assembly for country X

Do you know what company is “Facebook for country X?” Facebook is. (Except for in China, perhaps.) Which leads us to…

Don’t Say These Things

“90%+ of teachers hate their LMS/SIS/etc.”
And yet they don’t seem to switch. What does that tell you?

“It’s fully integrated. Plug and play… as long as there are APIs.”
So it works. If it works. Except when it doesn’t work. Gotcha.

“And we haven’t even started selling to parents yet!”
Yeah, that’s not hard at all…

“If we only get 1% of the market…”
Yeah, that’s not hard either…

“I created this because it is what my child/class/students needed.”
My follow-up question: “Is it what other child/class/students need?” If, after two years of cranking away, there are only a few dozen of other schools that are willing to pay to solve this same problem, most investors will lose interest very fast.

“We will get the teachers using the free version and then school will pay for it.”
Ah, no they won’t. Why would they when teachers can use the free version? It’s not surprising that a go-to-market strategy that avoids the pain of selling directly to a school administration by hooking the teachers and effectively deputizing them to drag the principal along appeals to a lot of founders. But figuring out where to put the paywall between free and premium is critical. The free version has to be useful enough to teachers that they will use it, but you have to keep enough value in reserve that the administration will make budget for it.

So now that you know how to make an Edtech investor cringe… please don’t. Take the time to pick the right concept and get it right. Then, we’d love to hear from you.

Author’s note: I’d like to thank all the people who contributed their ideas to this warning list… but most of them asked to remain anonymous (I wonder why?) so I’ll just say “Thank you all… and you know who you are” 🙂

The Brutal Economics of Running a Startup Accelerator

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

Startups, ever wonder what it’s like on our side of the curtain?

For the past several Julys, I’ve been going to Montreal to participate in Startupfest. Often, I address the startups during the main festival on the usual topics: how to find investors, how to solicit feedback on your startup idea, etc.

This year I spoke at the pre-festival “Acceleratorfest.” Held the day before the main event, it’s an opportunity for people who run accelerators to meet, share what works, commiserate with each other about what doesn’t, and generally learn from each other.

The topic they asked me to speak about was the economics of running an accelerator program. So if you ever want to know what keeps us up at night, here’s your chance:

The Brutal Economics of Running an Accelerator

The Three Dimensions of Pain (Points)

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

“You need to sell painkillers, not vitamins.”

I’m sure you’ve heard that one before. Vitamins are nice-to-have; painkillers are must-haves. Vitamins are hard to sell; painkillers are (relatively) easy to sell.

But have you ever really stopped to consider what pain is? It’s not as simple as it sounds. In fact, there are at least three dimensions of pain you should understand.

The first dimension is intensity. Is it a hangnail or did you just smash your thumb with the hammer? Because fixing a hangnail is never going to make your customers’ top 5 priority list. And given how time-starved we all are and how many excruciating problems we might have, most of us will never make it to item #6.

Most home automation solutions I see fall into this bucket. Turning your bedroom lights off from your office just isn’t a pain point for most people. The same goes for adaptive lighting solutions that vary brightness and color to fit our circadian rhythms better. While the health benefits are real, for most of us, a cup of coffee in the morning and manually turning down the dimmer at night seem to do the trick just fine.

One of the reasons Twist is so compelling is that it hijacks a real pain point with its wireless speaker embedded light bulbs. Wireless speakers rarely are genuinely wireless – you still need electricity – but Twist solves that problem by screwing right into a light fixture and gives you healthy lightning and the backbone of a home automation system as the cherry on top.

 

The second dimension of pain is prevalence. How widespread is this pain point? Many founders I meet are passionate about the problems they solve because they lived it themselves. This means they are intimately close to their customers… except when they are the outlier. If the pain isn’t shared widely, your market size deflates like a leaky balloon.

Find-a-roommate apps generally fall into this bucket. For young founders in cities like New York & San Francisco, this can be a real problem but it’s irrelevant to married couples and in most cities where the cost of living makes renting your own place affordable. Plus, most singles have friends so finding a compatible stranger isn’t necessary. ** It is a testament to how valuable intent to move data is that these apps get any attention despite the limited prevalence of the pain point.

** I wonder if founders who gravitate to these kinds of apps tend to be less socially connected?

Most of the civic engagement solutions I see also fall short on this axis. The founders are often very engaged in their local communities and don’t want to miss out on pubic hearings about zoning, municipal services, etc. Most of us just don’t care. The vast majority of citizens cannot even be bothered to vote in local elections.

What made PublicStuff and New York City’s 311 call-in service (now an app as well) successful was that they found local issuers that we all actually care about – fixing the pothole on my block, seeing if I can leave my car where it is because alternate side of the street parking is suspended due to some holiday I’d never heard of (but now suddenly love). These are prevalent civic problems.

The third dimension of pain is frequency. The classic edtech example is finding the right college. A near universal, massively intense pain point with lifelong repercussions… but it only happens once in a lifetime.

In real estate, the equivalent is services that make buying or selling your home more efficient or that help you get a better price. Selling a home is incredibly stressful and one of the largest financial transactions in most people’s lives, this is an 8 or 9 on prevalence and takes intensity to 11 but it only happens a few times in your life. The implication is that finding the customer will either be difficult, expensive, or both. This is why real estate brokers can pay over $100 per click to Zillow for leads on clients in prime zip codes.

So if your startup fails on frequency, you’d better have creative, scalable ways to acquire customers or ways to monetize those customers so much better than your competition that you can afford to outbid them.

Ideally, your startup scores high on all three dimensions. At worst, you score very high on two and have a sound plan to get around the headwinds caused by the one you are missing. But if you don’t, please do yourself a favor and go back to the drawing board. You’ll be saving yourself a world of hurt.

Business Etiquette: 4 Things That Mildly Annoy Me

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

Every morning I start my day with Dilbert & coffee and one of my favorite secondary characters in that strip is Phil, the Prince of Insufficient Light. Unlike Satan, Phil punishes people for small crimes by “darning them to heck”.

There are hundreds of articles in the business and startup press written about best practices and big mistakes to avoid, but surprisingly little about the small faux pas that, while they don’t immediately doom a relationship, will get you started on the wrong foot.
So in that spirit, here are four things that mildly annoy me and if you don’t stop doing them, I will sic Phil on you with his “pitch-spoon”.

1. No or uninformative subject lines
I know you think you get a lot of emails, but wait until you see my inbox. Anyone in the VC or accelerator business gets hundreds of emails each day from prospective startups, would be service providers, colleagues, portfolio companies – and that’s not even counting newsletters and personal correspondence.

Blank subject lines are like unattended bags at a train station; are probably not important but have a slight chance of being a bomb. You force me to open it just to be safe, when I have too many more time pressing emails to handle. Stop being lazy and toss me a bone here.

Meaningless subject lines are even worse. I can see you didn’t simply forget to use a subject, but how does “Hi!” help?

I’m a little less judgmental about ambiguous subjects like “Intro request” or “Follow up”. You are actually trying but don’t quite get it. When I’m staring at a screen with a hundred emails on it, how do I know what company or project this is about? If I’m later searching for this email, how can I tell at a glance that this is the right one? Consider these alternative subjects instead:

“X would like to meet Y (Co Y)”
“Follow up – Event Z, X (Co X) / Y (Co Y)”

These tell me at a glance who is involved. In the second example though, the event can be a phone call, meeting, conference, etc. and by including it in the subject you are giving me critical context.

Note: I’m not including misleading subject lines here because tricking me into opening your email crosses the line from mildly annoying to really pissing me off.

2. Poorly executed quasi spam
While we are on the subject of email, I’m getting a lot more unsolicited email for b2b services. Some masquerade as one to one emails but obvious lack of any clue as to what Dreamit and I do. This combined with the unsubscribe link at the bottom are dead giveaways. (Btw, if you are going to spam me, goddammit have the balls to commit and drop the unsub!)

At this point, I can even tell just by the formatting of the email that it’s a mass email. There is something about it that’s just looks to… formatted.

Some of these quasi spams even pretend to know me. They say things like “I’d like to follow up with you on…” as if it’s possible I’d suddenly remember a conversation we’d never had. Some claim to be connected to me through “a mutual friend” but when I reply asking who, there’s no one. A few even make up names of this mutual acquaintance.

Now, I meet a lot of people so it is possible that I don’t recognize the name right away but it’s not hard for me to check LinkedIn and search Gmail to get to the truth. I might let the first group get off with a quick Delete, but the pretenders made me think and for that, they get the Report Spam finger.

A refreshing few openly and candidly admit to being cold emails. If they are targeted (or lucky) enough to actually be relevant to me, I might even respond.

Note: One of these days, I may write a post on how to do the quasi spam right, but for now, on with my rant.

3. Generic Cold LinkedIn connection text
Would you go up to someone at a conference and say, “We should network”? Of course not. (Although, believe it or not, this did actually happen to me once.) You try to figure out enough about the target – from their name tag, where you are standing, any other scraps of context you can dig up – to lead with something that might, just possibly, interest them enough to want to continue the conversation.

So why on earth would anyone send a LinkedIn request to someone they didn’t already know with just the genetic “I’d like to add you to my network” message? If you have an idea why it might make mutual sense for us to connect, why not take the extra seven seconds to spell it out? Because if you direct me to crawl through your LinkedIn profile in order to read your mind, it ain’t happening. As you’ve probably noticed, I resent being made to think.

4. Calls without prior scheduling
Phone calls disrupt my flow. So if you call me without prior scheduling you’d better be my wife, kids, mom, or someone who I really, really want to talk to. Otherwise, you are one step below a Jehovah’s Witness knocking on my door. At least they care about my soul; you just want to sell me something.

Tip: if you are not sure, text me first. “Ok to call about xxx? Somewhat time sensitive” is not too much to ask for.

Please help make my days mildly less annoying by sharing this with the people you know who most need to read it… and I’m sure you know exactly who they are.

 

The Art Of The Exit: For Non-CEOs

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

Like most entrepreneurs, I wasn’t CEO of my first startup. While I had a fair share of the company, I owned far less than the CEO who, in addition to having had the concept, also initially bankrolled us.

For the most part, this didn’t matter. Like most good founding teams, we had complimentary skill sets and mutual respect so decisions were by consensus. This worked fine until one of us wanted to sell.

For context, the company effectively started in early 2000. We were hit hard by the dot com crash and one of the lesser casualties of September 11 was our term sheet. So we stopped taking even meager salaries and bootstrapped to profitability in 2002.

The next few years, we lived the dream. Ridiculously high growth, increasing revenue per customer as we upsold new modules, competitors folding. Fun times.

Nevertheless, by 2006 I wanted to sell. Six years was a long time but my decision was mostly about the trends. Our growth rate, while still high, had started to come down and the vibe at trade shows was that we were past the early adopters; still plenty of prospects but slower to sign. At the same time, our competition was trying to lure our best customers away by undercutting us. We were doing the same, of course, but once a steal becomes an attractive trade off relative to greenfield prospects, something fundamental has changed.

That said, our growth was still really, really good and the market was *hot*.  On the numbers, we could have got 6-8x times earnings. Plus, we had a good chance to attract strategic buyers and their valuations can get crazy (in a good way).

The CEO wasn’t interested. He believed that our new products would fix growth so we could get the same multiples on a higher base in another year or two. Knowing what we knew then, he might have been right.

But he wasn’t. Next year growth was a bit lower. Still really high but now we had two years declining growth. Uh oh.

So he agreed to shop the company. Unfortunately, the banker we brought in now thought we could get 4-6x earnings from a financial buyer but there were still strategics….

After a year leaving no stone unturned, the best offer we got was… 5.5x. No strategics. Between the market cooling, taking time to digest their previous acquisitions, and our growth slipping, they didn’t bite.

The CEO didn’t want to sell. I knew it would be years before he shopped the company again and, even when he did, the odds of getting a better offer hinged on an increasingly unlikely turnaround so I still wanted out. But I didn’t have a large enough equity stake to force it.

So I told the CEO that, if the prior offer was too low, he should be thrilled to buy me out at that price. I also told him that I was ready to move on even regardless. Ultimately, he agreed to buy me out in exchange for my finding and gradually training a replacement.

I got my final check on Jan 2, 2009. He looked me in the eye and said, “Maybe I should have sold.” Fast forward seven years, still no sale.

This clearly wouldn’t have been possible without the cash. Plus, were I not a core team member, he might simply have wished me well. Ironically, it wouldn’t have worked had I had more shares – another cofounder with more shares couldn’t exit for this very reason! Not enough cash to buy out his stake.

Lessons? 

1. For your first startup, a solid double or triple in a few years often beats holding out for the home run that may never happen. Life is a lot easier with a win under your belt.
2. Use inside information. If you’re seeing the road getting bumpy, act on it.
3. Don’t fill an inside straight. The irrational optimism that got you this far has no place here.
4. Respect the market. It may be hot now but it can change at any time. You wait on it; it does not wait on you.
5. Respect the market. (Yeah, I know…) Barring #2 above and filtering any of that through #3, if you ran a good process, the price you get is likely fair.
6. Governance matters. Understand who can stop or force a sale under various scenarios. You may not be able to change this, but you don’t want to be surprised.
7. Be creative. Not all exit doors are clearly marked.
8. Recognize your leverage – in some cases, weakness can be strength – and be willing to use it.

Now go be awesome.