Exclusive: Cyber-Security Guru Vlastimil Klima Talks Blockchain and Cryptelo

This week I sat down with the renowned cyber-security expert and co-founder of StartupYard alumni company Cryptelo, to talk about a topic we’ve covered a lot lately: blockchain, and security. 

We have informally dubbed Cryptelo. “The Unbreakable Dropbox.” You can also check out a previous interview with his fellow co-founder and CEO at Cryptelo, Martin Baros, or visit their website to learn more about their products.

Hi Vlasta, tell us a bit about your involvement with Cryptelo. How did you and Martin Baros start working together?

Martin actually came to me after encountering security issues himself. He wanted to create a secure storage solution that didn’t exist anywhere on the market.

As an entrepreneur, he had a natural instinct that caused him to seek me out. When he proposed the idea, I realized: “yes! Why hasn’t anyone done this?” I joined as his chief cryptographer, and together we built Cryptelo.

Cryptelo Co-Founder Vastimil Klíma

You have a fascinating background in Cyber-Security, and are named among the top cryptologists in the world. You’ve worked for the Czech government, and you were among the few to seriously break SSL as a whitehat. What drew you to cybersecurity?

As a little boy, I was a very good chess player and a mathematician in high school. I also took part in the International Mathematical Olympiad. Later, I learned/realized that since that point I had been watched by the “head hunters” of the secret service.

That sounds like something from the movies, but it really happens!

Once I graduated with a mathematics degree from Charles University, I ended up working for the state, in a secret department for censorship and cipher development. As I discovered later, there are many great mathematicians and participants in the international mathematical Olympiads working in the secret services of the various states.

One of the big attractions for somebody like me to this kind of work is the opportunity to solve very complex problems that no one else has done before. You have a sense of tackling the unknown, which is very rewarding.

In my work I dealt with the development of cipher and cryptographic devices as well as cryptanalysis. Later I was also in charge of the ciphers for our agents abroad. After the Velvet Revolution in 1989, I was entrusted with the development of ciphers independent of the Soviet Union.

For almost two years I worked for the General Staff of the Czech Army, and then I went to the private sector. The pearl in my story is that I did my first private-sector job together with Eduard Kucera and Pavel Baudis (nowadays Avast’s vice-presidents) for their company, which is now among the top antivirus companies in the world. I’m quite proud of that.

Then a number of security companies followed, for which I developed different cryptographic products or did security and cryptological analysis or cryptographic designs. Some time ago I worked for the Czech National Security Authority on the design of cipher and cryptographic devices already in operation for five years. I was very fortunate to have always been able to work with the most advanced technologies or even the “upcoming” technologies, both in cryptanalysis and in cryptography.

Let’s talk about blockchain. Today it’s often described as highly secure. As an expert, what is your view on this?

The “blockchain” concept is very good and very safe compared to other [data verification] concepts. It is based on distributed security and responsibility, which is great.

But it’s just one building block in the whole system. Much depends on the other parts of the system. Surely you remember the lesson that an attacker chooses the weakest link in the chain. In security, you are only ever as good as that weakest link.

 Vlastimil Klima, Cryptelo

Why is it that despite the integrity of bitcoin’s ledger, there are still so many bitcoin heists and thefts?

Bitcoins are based on the blockchain principle, but paying with them requires the protection of cryptographic keys. In all major world bitcoin thefts, these keys have been stolen. The thieves then simply transferred the bitcoins to their bitcoin accounts.

So this is something like building the most secure safe in the world, with keys impossible to copy and locks impossible to crack, but then having it breached by the thief simply taking the keys off your desk. The whole concept of the unbreakable safe is not much good if getting into it is so easy.

Let us note that there has been a shift in our collective understanding of security – we are not talking about cryptographic techniques, but only about keys, their creation, distribution and protection. In many respects, we have figured out cryptography quite well. Information can easily be made very secure in terms of encryption. But that does not mean we have “solved security.” Far from it.

People think of Bitcoin and other cryptocurrencies as anonymous. Is that a mistake?

Bitcoins may be anonymous, but they may not.

The advantage of bitcoins and other blockchain-based coins is that transactions with these coins can be verified. For the same reason, it is possible to see how the coins “travel” on different “wallets”.

If someone makes a mistake, you can determine who they are, and what they bought for bitcoins.

I worked as a forensic expert on investigating several bitcoin thefts involving illegal drugs and arms markets, and managed to prove who controlled the marketplace and who stole the bitcoins. These are not truly anonymous platforms.

If I’m a regular guy wanting to buy crypto-coins of any kind, how can I protect myself from theft?

Every security breach up till now has consisted of theft of cryptographic keys, which were inadequately protected.

Here comes the simple advice: protect your keys and do not give them to anybody else. At big markets and shops, it is common that you have to give them their keys to make deals for you. Here you have to be very careful, because the purses of the big stores are the most threatened. Just give them small amounts or at best trade peer to peer.

As a cryptologist, what are one or two ways you wish every software company would think differently about data security?

This is very difficult. We all do just what we have to do. It is natural that we do not perceive security as important until we become a victim of a security incident. I have experienced this myself, so I know what I’m talking about.

Most of the time, data security problems arise from a lack of time and money to do the work properly. And attackers choose just this kind of company to attack, because it is vulnerable. So the best defense against security breaches is to maintain a high standard – higher than your competitors.

Predators prey on the weak. As we say: the gazelle does not have to be faster than the cheetah, it simply has to be faster than the other gazelles.

What is Good Storytelling? (Part 1)

First: What is Storytelling?

There’s no single compact definition that can cover every modern use of the word “story.” You may think of news articles, or children’s fairy tales. You may think of “user stories,” that product designers use to figure out what to build. You may think of a novel. In fact, most stories have common characteristics: characters, settings, plot, conflict, and an ending.

But in talking about a “brand story,” or a “cultural story,” or a “life story,” we are really discussing a specific kind of story: the “Mono-myth,” also commonly known as a “Hero’s Journey.” At the heart of what we call “storytelling” in the modern world, you find this core structure:

The world’s oldest documented story is The Epic of Gilgamesh, written 4000 years ago on clay tabletsIt’s the story of Gilgamesh, a God King of the Sumerian state of Uruk. He begins as a restless and foolish young man, who leaves his city behind to explore the world, faces many challenges, becomes wise, and returns home a hero, ready to lead his people.

That ought to sound familiar. It’s the basis of every epic story from the Odyssey to Star Wars.

The Hero’s Journey works incredibly well at persuading audiences because it is a simple and flexible vehicle for conveying the human experience. It speaks to us about our experiences in life, by recreating those experiences, only with more flair, more danger, and bigger stakes.

The Hero’s Journey

Pick a big successful brand at random. Recall what you can about their “story.”

Chances are excellent that it is a “Hero’s Journey,” following the same pattern laid out 4 millennia ago in Gilgamesh. McDonalds has its Ray Krok, Apple has its Steve Jobs, and Microsoft its Bill Gates.

Not coincidentally, there are movies about all these characters, and they are all Hero’s Journey movies. The appeal of this story is so great that it is virtually synonymous with storytelling in film.

Within each of these stories is a familiar narrative: a misfit, naive and ambitious, confronts a cruel world, fails, grows, and finally succeeds. That is the simple core of every human story, and thus, every company story as well.

Qualities of a Great Story

Now we know what a story looks like. So which are the specific qualities of a really strong story? What makes this overall structure work best? Here are a few things I think are essential in a good story:

Great Stories Have Human (imperfect) Characters

Great stories appeal to the listener by being, essentially, about human nature. Great heroes are appealing because of their humanity, and not because of their power.

 

The 2010’s Most Popular Hero

Think about why people love Batman, or Iron Man: it’s because they are flawed human beings. It is the human experience to face moral tests and temptation. Thus, a story in which good and evil are too easy to separate is a story without any moral tension.

For Example:

You may have at some point spotted this meme making the rounds on Facebook. It’s got enormous viral potential, which is why it has been shared so widely (by both those who find it hilarious, and those who take it seriously)

It’s also a great example of bad storytelling.

In this story, we are presented with two characters in conflict: one entirely sympathetic and brave, the other entirely unsympathetic and cowardly. Thus, the point of the story, or the moral, is never in doubt. While the story creates suspense by making it unclear exactly what will happen, it creates no suspense over what the story thinks should happen.

No one in the story learns anything. No one changes as a person. One wins, and the other loses, but nothing is different at the end.

Great Stories Are About Change

I attended a panel on startups by the renowned actor Kevin Spacey this past weekend. One phrase above all stuck out to me as an example of how he sees storytelling. When asking a founder a question about his motivations in business, the founder responded: “Well, that’s complex.” To which Spacey responded: “Go ahead. Be complex.”

People are complex. So stories must also deal in moral complexity. They must give the heros and the villains an “arc.” As in Gilgamesh (or any epic story), the hero must fail to become wise. A villain must experience pride before the fall. Otherwise, nothing has changed.

Take, for example, this highly compelling commercial from none other than Budweiser, simultaneously America’s best selling, and worst tasting beer:

This is practically the definition of a Hero’s Journey. A young man with a romantic vision leaves home, only to find that the world is harsher than he expected. Enduring many trials, he finds help in unexpected places (the black man on the river boat). Having grown through his experience, he reaches his new home ready to accomplish great works: in this case, brewing beer.

This ad was seen as shockingly political (released weeks after the 2016 US Presidential Election), but it was also very successful. And that is because it is a real story, not just an ad.

It seeks to reframe the story of Budweiser, “America’s Beer,” into the story of Americans themselves, where they come from, and what they should believe in.

It also presents a coherent moral argument: that adversity makes us stronger, and that perseverance leads to success.

Importantly, neither of the two main characters in the story (America, and Budweiser himself), are either purely good or evil. Budweiser shows hints of arrogance from the beginning, before becoming wiser, and America shows signs of openness, even after initially seeming a cruel place indeed.

The story is about these characters changing together.

Great Stories Are About Conflict

As we’ve now seen, conflict is essential to a powerful story.

Conflicts in stories boil down to need. Human beings and societies have competing needs. How those needs are addressed, and which needs win out over others, are key elements of a story.

Convincing an audience that one need is greater than another is vital. Otherwise, why should a person pay attention to your story? It involves no consequences.

This is a video I often use to talk about bad storytelling. It’s a coca-cola ad from the early 1980s, when Coke was getting its ass kicked by Pepsi’s brilliant marketing.

But what’s not to love? Sunny day, happy people, soccer for some reason, and everyone having a “Coke and a smile.”

This ad was a failure, along with much of Coca-Cola’s marketing at the time. There is zero conflict in this story. And because there is no conflict, there is no identification of any urgent need. Do I need to have a coke on a nice day? It seems these people are having fun, regardless of what they’re drinking.

Brands routinely fail to introduce real conflict into their product and brand stories. Here’s a more recent example:

 

There’s a lot wrong with this ad, but the most important problem is that the conflict it presents is false. We see trials and struggles for the hero, but we are told at the end that there is no solution. And instead we should just buy a car. It’s insulting.

Cowardly marketing and bad storytelling happen when we refuse to acknowledge that our customers are people with their own problems. They aren’t just people out in a park having a perfect day, ready to jump at the chance to buy a coke.

They won’t automatically feel better about themselves just because someone tells them it’s ok to buy a car. Even if that car is the best car ever. They have other needs as well- more important ones.

Coke actually learned that lesson. Here is a typical ad from more recent years:

Here is conflict. Suspense! Competing needs and wants. And the brand in the story is associated with wisdom, with the setting aside of personal enmities in favor of love.

That’s a great story to tell. It appeals to people as they are: always in conflict with themselves, and always unsure of what is right.

Creating and Resolving Conflict

How do you make your story real to other people? You do it by making the conflict real to them. By showing them how the conflict in your story should matter to them.

This is also where a lot of startup stories fall apart. They make the mistake of thinking that making a good argument is the same as actually persuading someone. But it is never enough to just be right. The person has to believe you’re right.

In the next post in this series, I’m going to talk about how to identify parts of your story, as a founder, as a company, or as a person, and bring out the hidden conflicts that will help you relate that story, and make it matter to other people.

ICO

ICOs: 2017’s Biggest, Most Misunderstood Trend in Tech

It seems like the tech investment market hasn’t been this excited about anything since 1999. The ICO, or “Initial Coin Offering,” is on the lips of every investor, and floats to the top of every startup discussion around fundraising and new business models.

Depending on who you ask, it’s a revolutionary shift in the investment paradigm that will help tech companies and investors alike become wildly rich, or it’s a scary bubble-creating, fraud enabling monster the likes of which hasn’t been seen since the dot-com bubble.

So what’s going on? What’s an ICO? What do you need to know about them? Why should I be wary or excited? This post will jump into the circumstances that created the phenomenon of ICOs, and try to dispel or confirm some of the most important common beliefs about them.

First, a bit of history:

First There Was Blockchain

In the distant technological past, around 2009, an idea emerged from a mysterious coder with the pseudonym of Satoshi Nakamoto. In a now-legendary whitepaper, he produced a theoretical model for a new kind of digital currency: what he called Bitcoin.  

Without getting too deep into the technology, the key to Nakamoto’s innovation was the idea of a distributed digital currency that relied on a network of computers to process and authenticate transactions for its users. This network would create many copies of a “blockchain ledger,” and would copy transactions written to the ledger based on consensus with the network.

The ledger would contain many “coins,” or unique pieces of code that could be “traded” from one user to another only with the use of a private key. Over time, the system itself was designed to create more coins as a reward for those who processed transactions- a process called “mining.”

In this system, transactions would be theoretically tamper-proof. The system would keep what amounts to a never-ending record of everything it does, impossible for one person to alter alone.

Though Bitcoin’s exact origins and Nakamoto himself are mysterious, what is true today is that millions of people around the world have traded bitcoins, and used them for a variety of purposes, including making payments, transferring money abroad, and in some cases, illegal activities such as extortion, money laundering, and black market sales. There is such ongoing demand for bitcoins, that they have been valued by some exchanges at up to $5000 dollars recently.

The popularity of Bitcoin has spawned many follow-ups, including and especially Ethereum, which has presented a number of technical advancements to solve limitations in the original Bitcoin technology, particularly Bitcoin’s lack of speed and extensibility.

Today, the Ethereum blockchain functions as a platform upon which applications that need a distributed blockchain can be built. The Ethereum coin called “ether,” can be “spent” as a way of leveraging the network on which it runs to accomplish new tasks in a secure way.

Blockchain and ICOs

While Bitcoin popularized shared ledgers, new platforms like Ethereum promise to put that technology to much broader use, such as in authenticating contracts, securing communications, and enabling new forms of crowdfunding. Proponents see Ethereum and similar technologies as a way to decentralize many functions of the web, and eventually the whole economy.

TechCrunch has a good introductory article on some of those ideas. I suggest you read that as well.

An ICO is one of those new uses of a shared ledger. As simply as possible, it is the process of offering a new set of coins for purchase, either for cash, or more commonly, in exchange for cryptocurrencies that the seller of the coin can then exchange for cash, or something else. The coins being sold by the company raising the IO should be tied to some external financial instrument or physical asset, such as a loan, a share of common stock, a security, or in some cases, “credit” towards the use of the products a company offers.

You may recognize this kind of transaction as essentially similar to the sale of a security or a debt. The main difference is that the sale is accomplished using a blockchain ledger, and the “coin” sits in place of a typical security instrument, such as a bond, or a note.

Thus, an ICO could be used to facilitate many existing business activities. It could be used to enable a group of lenders to pool their money, or it could be used by a startup to sell equity in itself. An ICO can also be used by an existing company to offer a way of buying its services (the same way mobile gaming companies sell tokens, gems or other items to their players to make in-game purchases).

The advantages of employing blockchain technology in these circumstances are the same as ever: increased security, transparency, and auditability. In short, ICOs can potentially offer a better or fairer way of doing things people mostly already do.

So Why is this So Crazy Popular?

Because it’s so easy to setup, and easy to use. The wild popularity of ICOs in the past 6 months or so is largely driven by the general investor hype around cryptocurrencies. As the prevalence of shared ledgers grows, it becomes ever easier to leverage them for novel purposes like an ICO.

And that cutting-edgness can make the ICO market a bit frothy and potentially bubble prone. People who have invested in cryptocurrencies, and more importantly those who missed the huge easy gains that early Bitcoin and Ethereum investors made, now are seeking more opportunities to make returns of a similar scope. At least a part of this is mania and greed, as evidenced by the wacky valuations and amounts raised in some ICOs.

On the other hand, ICOs carry undeniably attractive advantages. They can be bought into from anywhere, by anyone, and are instantaneous- a powerful antidote to the slow and restricted nature of traditional investments and bank transactions for end-consumers. In a sense, an ICO lets individuals do what big investment banks have been able to do for decades: to be the first movers in new and exciting markets.

What an ICO is Not

Of course, that freedom and opportunity comes with its own cost.

Currently ICOs are mostly considered to be unregulated, and have thus been characterized as dangerous, risky for investors, and legally questionable by experts. Certainly those ICOs which mimic the characteristics of a classical IPO have been among the most concerning activity in the ICO market, and were the primary motivator for both the Chinese and US governments to intervene in the market recently.

An ICO can allow a company to bypass institutional investors who might normally help to diversify risk for consumers, or ensure that an investment is legally structured in a way that protects investors. In an ICO however, no central mediator such as a stock exchange or investment bank exists, and thus, in some cases, due diligence on behalf of investors is poor or non-existent.

Whatever the legal or ethical dangers, ICOs have quickly ballooned in value to what is estimated to be billions of U.S. dollars in the past year. Companies have used ICOs to raise eye-popping amounts of money, sometimes with little reliable information about where that money is going, and often with little legal protections in place for buyers.

ICOs have also been the tools of purely criminal enterprises, with a fraudster reportedly caught attempting to move $350 million of ICO investments offshore from India, after a fake ICO for a company calling itself OneCoin.

Massive speculation in cryptocurrencies has fueled plenty of fraud and abuse from bad actors looking to make easy money. And the distributed nature of a shared ledger makes it correspondingly difficult for investors to organize in response to problems. Collective shareholder action becomes difficult when many shareholders remain anonymous.

As to whether we are in a crypto bubble, as many commentators fear, it is inherently difficult to recognize a bubble when you are in it. But according to the economic historian Michael Lewis (author of The Big Short), a defining feature of the investor mania that leads to bubbles is “ an exponential increase in the volume and complexity of fraud.” And fraud today in crypto-currencies is both voluminous and increasingly complex.

Original Art by Mirek Sultz Copyright 2017, StartupYard 

Are ICOs Legal?

At least right now, they’re not illegal in most places. But the question of their legality is part of an evolving situation. They have recently been banned in China, as the government grew concerned over the disruption they were causing in the country’s traditional financial markets. In addition, the SEC (Securities and Exchange Commission of the US), has also issued new guidance suggesting that ICOs that are similar to a classical IPO must register with the SEC, and adhere to existing regulations.

The ESMA (the European SEC), has yet to issue coherent regulatory guidance for European investors and companies. European regulators are typically slower to act than either the US or China.

In addition to this, while an ICO might not be illegal, it may in some cases be technically illegal to participate in it. For example, investors who are American citizens, and the companies they buy coins from, may be at risk of violating US laws including FATCA and FBAR – laws that require many financial transactions to be reported to the US Government when they involve American citizens.

In most countries, ignorance of such laws is not a defense for breaking them.

Are ICO’s Safe?

They can be. An ICO is not inherently safe as an investment. One unique risk in blockchain transactions, as opposed to traditional commerce, is that nothing is reversible. “No backsies,” meaning that you can’t appeal to anyone to recall a transaction once you make it.

And a coin alone does not guarantee shareholder rights or ownership of something. However, if the proper legal framework is used to tie coins to real assets or give their holders certain rights, then an ICO investment or a coin purchase is not fundamentally different from the purchase of any other type of security or medium of exchange.

So while an ICO is not by definition “safe,” it is not necessarily any more dangerous than any other type of transaction. And in some ways, it can be considered more secure against certain threats.

Ok, but Should I Buy Into an ICO?

According to our in-house blockchain expert, Decissio founder Dite Gashi, you should not consider investing in any debt or equity ICO unless it meets some essential criteria (many of it the same as for any traditional investment).

Here are the highlights of Decissio’s checklist:

  1. The ICO’s Focus – The focus should be on the business, and not on providing investor returns, particular fast investor returns. If it looks like a pyramid scheme, assume it is.
  2. Meeting Technical Due Diligence – either you or someone you trust has examined the technical specifications of the offering, and are satisfied that it is sound from a technical point of view.
  3. Complete Company Documentation – Just as with any investment, the company launching an ICO should be on a sound legal footing, and should be represented by qualified board-members, free of legal trouble, compliant with regulations, and have its finances in proper order. If documentation that establishes this is not provided, then the investment may not be as safe as you think.
  4. An Exit Plan – A company raising money through an equity or debt ICO should have a clear idea of how and when investors can be paid back, what triggers a liquidity event, what events or milestones call for a reorganization of the company, and so forth. This should all be provided in writing and vetted by your own legal counsel.
  5. Legal Framework – Purchase of a coin in a debt or equity swap absolutely must have legal documentation tying the coin to a real asset, or to the right to collect payment on a debt. Sufficient collateral for such a transaction should be in place, and all standard legal documentation must be provided. The blockchain technology does not replace any of this, or make any of it less necessary.

To be clear: we are not offering financial advice. But our opinion is that an investor should make a habit of looking for the same kinds of things in any investment they make. The way that an investment is offered doesn’t change the fundamentals of wise investing.

As the renowned VC Fred Wilson says: “Don’t be greedy.”

Should I Raise an ICO as a Startup?

In answer to this, we would pose a different question: what are the specific advantages of doing an ICO?

  1. It’s Faster: ICO might be easier to manage in the long term. Because it’s handled using a shared ledger, there’s no need to deal with many investors all trying to give you money at the same time- no problems with exchange rates, transfer fees, bank delays, and other annoyances.
  2. It’s more Scalable: Unlike a typical early-stage investment, an ICO can in theory be easily extended or replicated in the future without any changes to existing agreements. Traditional equity investing involves complex time-intensive processes to transfer shares, convert notes, gather signatures, and the rest.
  3. It’s Auditable: A nice thing about an ICO is that it can all be audited. Investors can feel more secure because a company cannot easily lie about how much money it has raised, or at what value. It’s all in the ledger.
  4. It’s Flexible: an ICO can be used by a small group of investors, just as it can a large one. This means that you can theoretically offer early investors the advantages of using a shared ledger, without sacrificing the personal touch that is so important with early stage investments. Startups rarely just need money: they usually need investors who can help them. It’s still possible to do that with an ICO.

ICOs are a Threat to Traditional Investors

It should be obvious by now that blockchain technology and ICOs are perceived as a threat by many traditional investors. And with good reason. Traditional startup investors may offer more than just money, but money is certainly a huge part of what they offer. ICOs can be a way to get around large institutional investors and deal with people on a peer-to-peer basis, meaning that traditional investors will have to compete harder for investments, and offer more to companies they invest in.

Early stage investors like StartupYard also face challenges from this technology. As it becomes easier to get capital from anywhere, startups are perhaps less likely to think of an accelerator as a starting point for their business. They may find that raising money in an ICO is easier – maybe even too easy.

Investors down the line may also find that investing through traditional institutions doesn’t give them the access to deal flow that they want, and they could be attracted to ICOs as a way of getting “closer to the action,” and giving money directly to exciting startups.

Tech Business Angels and VCs may also find that startups are not as keen to cooperate with them because of the alternatives available. That may be good for some startups, and very bad for others. Small companies that raise money too quickly often make big, costly mistakes, rather than little, cheap ones. Institutional investors don’t make you immune to that problem either, but they can enforce much needed discipline on founders who are playing with lots of funds for the first time.

What can we do about it?

As the famous line from newspaperman Horace Greeley says: “Go West, young man, go West.” In other words: we must adapt to our times. The reality is that this technology is gaining popularity because it promises something that people want: a new level of transparency and immediacy, for investors and for startups, that the old investment world can’t match.

While we have to continue to advocate for the processes that have made us successful at what we do (which have less to do with money) we also have to recognize that the modes of technology change whether we want them to or not. Our model must adapt, which is one of the reasons that StartupYard has made itself available to smaller investors through private equity placements over the past two years. We see that small investors want more access to early stage investments, so we must provide it in a way that makes sense for us, and for them.

Still, and it bears repeating: startups don’t really need money as much as they need help. Really effective startup investors provide enough money, in order to offer the level of help a startup really needs. A day may soon come when StartupYard will adopt blockchain technology in our own fundraising efforts. But when the winds of change blow, you shouldn’t be blown away by them. At the end of the day: the tech business has to be about more than money.

Mentorship

Is Mentorship Like a Game of Chess?

Today our Batch 8 startups will begin to meet with mentors, a process that will take around a month. They’ll have nearly 100 45 minute meetings with mentors from diverse industries and specialized backgrounds.

So how do we prepare startup founders for getting the most out of this crazy rush of meetings? Simple: we give them tools, and training on how to use them. Pro tip: start with David Cohen’s Mentorship Manifesto.

The First Best Tool: Positioning

The thing we focus on first with our startups is “Product Positioning,” which we’ve also written about extensively on the blog. In short, it’s the art of framing your work in a context that others will immediately understand, accept, and sympathize with. A position statement details the target customer, what their problem is, how you solve their problem, what their alternatives are (your competition), and how you’re different.

We strongly believe that starting mentorship sessions with a positioning statement is key to getting the maximum possible value out of mentors. It sets the ground rules for a conversation at the outset: helping a mentor to understand what your basic assumptions are about the world and what you’re doing, and letting them know what you’re working on, and what you know about the business you’re in.

Mentorship as Chess

Mentorship can be thought of as like a game of chess. There are two players, they are equally matched, but one must move first. Both know the rules, but neither understands the thinking or tendencies of another before the game begins. The game is limited to the pieces on the board. Slowly, by making their moves, the two players reveal to each other what is important to them. Every move has an answer, and you don’t stop until one of you is out of moves (or time is up).

Of course, mentorship isn’t a competition, but then in some ways, neither is chess. It’s an exercise in controlled, directed communication. That is what good mentorship is: a focused, stripped down form of conversation that teaches two people about each other.

In this light, mentorship can be seen as a process you can optimize and perfect. You can get better at it over time.

Here are some steps to do that:

Step 1: Setting the Board

Mentorship

Rather than sit down across a table from a mentor with nothing to say, and no plan for how the conversation should play out, the founder must “set the table,” often with a pitch, or a positioning statement.

Setting the conversational agenda is a vital step, and there are many ways of screwing it up. One of the ways founders fail at setting the agenda is by refusing to lead. Rather than come out and state what they do, and what they want to talk about, they will bite around the edges. They will delay, and distract, rather than getting to the point.

And this happens because of fear: fear of failure, or of looking stupid. That fear leads founders to try and push the focus of the conversation away from themselves. Sometimes they try to start with “literature” such as an executive summary or a pitch deck or video, as a way of easing the pressure on themselves. But this is usually a mistake, because the opening of a conversation is about “setting the board,” and bringing a mentor’s attention to the topic you want to discuss. While a pitch deck or a video might be interesting, but it’s also impersonal. It isn’t you. This would be sort of like inviting someone to play chess, and then asking them to critique your outfit. You are a living mind, not a pitch deck.

If the first thing you show someone is a presentation, then more often than not, the whole conversation becomes *about* the presentation, or video, or whatever it is. Rather than engaging with ideas, a mentor reacts to things they are shown: they react to what they see, rather than what they are asked to imagine. This limits the conversation, and usually wastes time and energy.

Like in chess, getting the focus of the other player to the center of the board (and away from your side of the board), is critical to controlling the game. If you start out offering your work to a mentor for a critique, then the rest of the “game” is played on your side of the board. This is how mentoring sessions turn defensive and counterproductive.

Step 2: Following a Strategy

Mentorship

As conversations have many layers, so too does chess. There are tactics, such as using combinations of pieces or positions on the board to accomplish tasks, and there is strategy- the way you pursue your overall goals by using certain tactics instead of others. Just as in a conversation, the tactics you use are superficial: a certain combination of words or a way of speaking. Jokes are a conversational tactic. So is eye contact. But these are not strategy.

Often we confuse tactics for strategy. We talk about the superficial aspects of conversation: how to talk to people, and how to please them. But ingratiating yourself is one thing, and getting what you need from a mentor is something else.

Your strategy is more premeditated, and it requires planning. How will I win this person to my way of thinking? How will I talk to them in a way they will understand and sympathize this? We do not achieve very effective conversations by relying on charm and wit alone – those are only tactical elements. Really good mentoring only happens when the founder plans ahead, thinking carefully about what they want from the mentor, and about how they are likely to get it.

Having a good strategy means gathering intelligence about the mentor you’re talking to, having an outcome for your conversation in mind (the thing you want the mentor to give you or do for you), and understanding what it is the mentor wants from you. Why are they mentoring you? What do they stand to gain from you?

All these questions can be asked before hand, but often are not. Some founders never engage in a clear strategy, and so they simply chat with mentors, never really getting anywhere. They try to be liked, rather than to earn respect and attention. Don’t make that mistake: having a “nice” conversation, and really getting something out of a mentorship session are not the same thing.

Step 3: The Endgame

Mentorship

Chess also has an end. Or rather, it reaches a point at which there is nowhere to go. That is the nature of the game, and to some degree, it is also the nature of a productive mentorship session. Knowing when you should stop is as important as knowing how to start. But often founders begin to repeat themselves, or to delay the end of the interaction, either to try and make a good impression, or just because they don’t know how to cut themselves off.

Sometimes too, mentors like to talk. I am guilty of that as a mentor, and I rarely end a conversation myself. If the person I’m talking to is very interesting, then I don’t always want to end it. But then that is about what I want as a mentor, not about what the founder needs. Thus, I do notice when founders are unable to break away and close the discussion. If the conversation takes on an air of inevitability, then don’t drag it out. Don’t get repetitive.

By having clear goals in advance, you’ll be more able to decide when and if those goals have been achieved, at which point you can conclude the conversation, and move on to other things.

As in starting a conversation, there are tactics for ending them. For example, you can shift gears by summing up your talk, and then clarifying the next step both parties are going to take. You can also frame this as a kind of question: “So, we’ve talked about the challenges in selling my product, and you’ve given me some great advice. Now I’m going to be implementing that advice, and I’ll let you know the results about 2 weeks from now. As you mentioned, you’re going to connect me with your contact at company XYZ. Shall I email you a reminder tomorrow morning?”

Then it is only for the mentor to either add something, or agree with the summary and plan. The conversation has been effectively closed, or pushed nearer to finishing.

Know too, the signs of a mentor who is done talking to you. If they begin to summarize your meeting before you do, follow along, and either confirm what they say, or add what you need them to remember. Always agree on what happens next, even if what happens next is “I’ll see you around.” You won’t need to follow up with every mentor, but make a habit of stating what your intention is. If it is not to stay in contact, don’t tell them you will. If you plan to contact them soon, then tell them this too.