Do you have what it takes to build a unicorn?


Sean Wise has an eye-opening article on This Study of 195 Billion-Dollar Companies Found 6 Counterintuitive Truths About Building a Unicorn, After 15 months, 300 hours and 100 charts, here is what researchers discovered about creating billion-dollar startups.

I’m going to list the six success factors in building a unicorn, adding a few comments of my own about how these findings relate to both mentors and founders. What is not addressed in the article, which I think is important for the vast majority of entrepreneurs who don’t build unicorn companies, is are these same factors key to creating a valuable company, just not one valued at a billion dollars or more?

Ali Tamaseb, a founder turned venture capitalist at Data Collective VC, gathered data on 65 key factors from all 195 unicorn startups based in the U.S. His work included all startups since 2005 that have publicly reached a valuation of more than $1 billion. The least surprising finding is that almost 60 percent of billion-dollar startups were created by serial entrepreneurs. In fact, he found that 70 percent of billion-dollar founders were “superfounders,” or founders with at least one previous exit of more than $50 million.

1. Industry knowledge isn’t required.

Certainly this is contrary to the received wisdom. But just as interesting to us mentors is that 80% of founding CEOs in healthcare and pharma had direct experience in their target market. Mentoring groups often reflexively bring in additional mentors with direct industry experience once a startup emerges from the very initial stages of company formation. From the study’s findings, this is only necessary in two verticals, which are closely related, healthcare and pharma. Unfortunately, neither Sean Wise nor the researchers speculate on what it is about these two verticals that requires domain expertise. My guess is that both are heavily regulated industries – see my post about the fourth risk – and that domain expertise is needed to navigate the complexities of government regulation. You don’t learn that in business school nor by doing a startup in an unrelated vertical.

2. Technical CEOs aren’t necessarily more successful.

I heard a great quote from an MIT VMS mentor the other day: “It’s not the technology, its the psychology.” Meaning that the customer and their psychology is what is decisive about a venture’s success, not the novelty or even value of the technology. This does not fly well at MIT, otherwise known as the Massachusetts Institute of Technology. Virtually every founding team is either all engineers or engineering dominated. So again, this finding is very helpful to mentors as we help founders build their team. This finding that successful tech founders vs. business founders are a 50/50 split was also found to be true of the author’s VC fund, Ryerson Futures.

3. You don’t need to be capitally efficient.

I was trained by the many VCs involved in my four VC-backed startups to “stretch the dollar” – they demanded capital efficiency, but only to a degree. As one vc told me, “Steve you’re going to waste a million dollars in this venture, but I don’t know which million, and that’s ok.”  According to the study less than 45 percent of unicorns were capital efficient. This certainly jibes with my reading about vc-backed startups – vcs are willing to put hundreds of millions into companies they believe will ultimately scale and go IPO, like Uber. This doesn’t mean that mentors should tell founders to be profligate in their spending, but only reinforces the “Nail it, then scale it” maxim. The function of external capital is growth and scaling, not creating product/market fit.” So I would say you need to be capital efficient until you reach product/market fit, after which you can focus on adding fuel to your rocket to gain escape velocity.

4. It’s (usually) not OK to be a copycat.

It’s no surprise that more than 60 percent of unicorns had a very high level of differentiation compared to incumbent firms. The worst strategy is copying what another startup is doing, especially if that startup is well funded. As a mentor I do preach differentiation and I believe that is the received wisdom.

5. You don’t have to be first to market.

Being first to market was a popular catch phrase and strategy in the dot com boom. Since that time few people I know see it as a formula for success. However, what the study found is that the best markets for billion-dollar startups already have a number of large incumbents, and often the startup uses the inefficiencies of these incumbents as a point of disruption. This is really important! What it tells me is that the size of the market opportunity is very important, but being first to  that large market is not. In fact this finding jibes with my belief in the maxim “No competition, no market.” Founders need to concentrate on large market and should not be discouraged by the presence of large incumbents.

6. You don’t need to be part of an accelerator to be successful.

The most dominant success factor in billion dollar market cap companies is that 70 percent of the founders were co-called “super-founders” – founders who with at least one previous exit of more than $50 million. This isn’t surprising. So if you aren’t a super-founder you may well want to apply to an accelerator. See my post Should you join an incubator or accelerator?

This article and the study upon which it is based provides very useful information for both founders and those that mentor them, regardless of whether the intent of the founder is to build a billion dollar market cap company or not.


Everybody’s talking about gender, but no one’s talking about class

aston martin

As the father of two daughters, I’m glad to see greatly increased awareness of discrimination against women in the startup world and some progress in leveling the playing field. A lot of focus is on the fact that there are far fewer female founders and it is far harder for those founders to raise capital than it should be. Research is demonstrating that more diverse teams make better decisions than the typical mono-cultures found in the startup world of young white males as founders and middle-aged white males as investors.

But what I haven’t seen addressed, and frankly I have to admit to not thinking too much about, is the very small number of founders who come from lower socio-economic levels. It wasn’t until the end of The Boston Globe article An upper-class mindset doesn’t make you classy that that the reasons for this surfaced:

…,the predominant US upper-class view of rules is that they’re made to be broken. Just look at popular books about success, like Marcus Buckingham and Curt Coffman’s “First, Break All the Rules” and Angela Copeland’s “Breaking the Rules & Getting the Job.” If we want to succeed, these books tell us, we’ll need to cast aside established social norms and chart our own path. This is sage advice for people who have little threat, but clearly bad advice for the working class.

Though they tend to shun rules, the relative looseness of the upper class offers several strengths: they tend to be much more creative, entrepreneurial, and open-minded. The working class, meanwhile, struggle with diversity: they are more suspicious of people who are different from themselves, who appear to threaten their sense of social order.

In today’s digital economy, several attributes of cultural looseness reinforce upper-class advantages. Whereas those from tight groups understandably tend to view change as a threat, loose communities see mainly opportunity. They have the cultural reflexes — socialized from a very early age — to adapt to disruptive changes, and the autonomy and independence to chart their own course.

Unfortunately the article’s author, Michele Gelfand, a professor at the University of Maryland, and the author of “Rule Makers, Rule Breakers: How Tight and Loose Cultures Wire the World”  and Jesse Harrington, a research associate at Fors Marsh Group, don’t offer any solutions to this problem.

Their conclusion, We must recognize that it’s culture that we need to reckon with, not just our bank accounts is not actionable information

However, one of my VMS colleagues is a mentor at an accelerator called Smarter in the City. Their mission is to bring diversity to Boston’s tech landscape:

Our mission is to diversify Boston’s startup sector by providing support and resources for local minority-run ventures. Through our accelerator program, we draw investment to communities that have traditionally been left out of the high-tech startup scene.

Check out the stats on minorities in Boston on their home page, they are eye opening!

9.2% of tech industry employees are Latino and African American

0.2% of venture funding goes to black women

20% of firms are owned by minorities

$8 average net worth of African-Americans in Boston

Supporting incubators and accelerators in the lower socio-economic areas of high tech-centric cities like Boston is one way to attack the lack of diversity. But I think this problem needs to be addressed earlier in lives of potential founders. Why aren’t there classes in entrepreneurship in the Boston public schools? Clubs for budding student entrepreneurs? Business plan competitions in high schools? In other words, young people across the economic spectrum need support, training, and encouragement to explore creating their own businesses. Unfortunately our public schools are still stuck in the 19th century model of churning out compliant workers for industries’ assembly lines. But until there’s real change in the antediluvian public education system, investors who have made a lot of money betting on entrepreneurs who look like them should direct some of their massive profits to support organizations like Smarter in the City. I don’t see a single VC firm or angel group listed amongst the sponsors of Smarter in the City. Though kudos go to Microsoft as the sole tech sponsor.





What’s the difference between coaching, mentoring and teaching?



Unfortunately the term “mentor” for startups is getting like “organic” for food: once meaningful, but through both misuse and overuse becoming close to meaningless. I have a post from a video by entrepreneurial guru Steve Blank that very clearly describes how mentors differ from not only coaches and teachers but advisors as well.

Thus I was pleased to see the Inc. article Do You Need a Coach, Mentor, or Teacher? Finding the right source of counsel makes all the difference as Inc. has a lot of reach with SMBs and entrepreneurs.

Here’s their very brief but helpful clarification between a teacher, a coach, and a mentor.

  • teacher is someone who has studied a topic enough to be able to teach what she has learned to others.
  • mentor is someone who has experience in your industry creating success for herself and can show you the way.
  • coach is someone who can help you with the internal aspects of entrepreneurship, personal growth, setting goals, and facing fears and resistance.

Another difference worth noting is that taking a course or hiring a coach typically costs money, where as mentor is synonymous with “volunteer.” I’ve yet to see any one charge for mentoring. If you do that you are an advisor.

Another point mentioning is where in your entrepreneurial journey you should look for what type of help. Typical is taking a course related to entrepreneurship, as many of my MIT students do before they enter the startup world via MIT Sandbox or one of the Institute’s many other entrepreneurial programs. By entering a support system like Sandbox or The Venture Mentoring Service founders get access to mentors. It usually isn’t until a venture is further along that coaching comes into play. Mentors or often investors may recommend a coach, usually to help a technically-minded CEO improve their business skills. Years ago we used to call this “going to charm school.”

Another way of looking at these sources of support is that the further along your venture is the more your need for domain-specific mentoring, advising or coaching. Very early stage ventures can benefit from mentoring on the many general issues common to all startups: what type of business entity to form, founders’ agreements, building a team, creating pitch decks, prepping for business plan competitions, etc.

An important point for founding CEOs: you need to differentiate between support for your venture and support you may need as a first time CEO. This is similar to the legal counsel issue: while ventures always have legal counsel often founders or executives can benefit by having their own attorney.

Taking advantage of the right teachers, mentors, advisors and coaches can be as important to founders as the talent they recruit. As I’ve said many times, startups are learning machines and founders should seek out sources of learning wherever they can find them, including their own staff and colleagues at other startups or even at mature ventures.


Telementoring in healthcare


An email alert I have for “chronic pain” generated a result for “telementoring.” Evidently that’s the term for virtual or remote mentoring that is used in medical care. However, unlike virtual mentoring or in fact any mentoring for entrepreneurs, the medical world takes a scientific approach. That translates into studying the efficacy of telementoring.

Telementoring is now regarded as a best practice in pain management and safe opioid prescribing according to the article Pain Management Telementoring May Cut Opioid Prescribing on the site Clinical Pain Advisor.

The researchers found that primary care clinicians participating in ECHO Pain (telementoring had greater percent declines than the comparison group in annual opioid prescriptions per patient (−23 versus −9 percent), average morphine milligram equivalents prescribed per patient/year (−28 versus −7 percent), days of coprescribed opioid and benzodiazepine per opioid user per year (−53 versus −1 percent), and number of opioid users (−20.2 versus −8 percent).

So what is telementoring, how does it benefit hospitals, and what does this have to do with mentoring of entrepreneurs?

And what problem is telementoring solving?

Today, experts estimate that all human medical knowledge doubles every 18 months. The pace of progress in surgical innovation is so fast that some surgeons have expressed serious concern about patient safety as technology diffuses throughout the real world without proper training.

Keeping your organization up with surgical innovation is imperative for growth, but surgical programs can be slow to adopt because surgeons are worried new technology may result in poor patient outcomes early in the adoption cycle. Because of these fears, some providers are seeking out telementoring.

An article provides some answers:

[telementoring] is procedural guidance of one professional by another from a distance using telecommunications, such as audio dialogue and video telestration (video tablet and pen). This valuable tool can help your surgeons and clinical teams feel comfortable adopting the latest procedures.

It’s clear that telementoring is a form of peer-to-peer education in the medical world. Surgeons are the early adopters. Telementoring reduces travel time and time away from work for the surgeon and provides expert counsel on the latest surgical procedures. Telemementoring has been embraced as a form of continuing education/training for surgeons.

The article concludes with this takeaway:

Telementoring should be on your radars as you think through how to boost adoption in your surgical service portfolio. While medical centers with access to advanced OR technology will likely lead the way, telementoring can reduce barriers to surgeon upskilling for all types of hospitals by lowering associated costs and improving surgeon comfort.

My takeaway is the telementoring could be used as a peer-to-peer training in domain specific areas critical to the success of a startup: how to get your venture investment ready; how to use social media to market your product; how to build your cap table and financial statements; and how to raise capital. Perhaps current in-person seminars for entrepreneurs could increase their reach and impact by adding telementoring. MIT Venture Mentoring Service has seminars in sales, marketing, and human resources.

However, telemarketing needs domain specific mentoring expertise and new and different guidelines for both mentors and mentees. Building up a network of telementoring experts seems like a natural extension of accelerators and incubators. This is especially true for market-specific incubators, such as focused on fintech and healthcare. A more rigorous program of both mentor selection for domain expertise and a more structured program of mentoring will differentiate telementoring from virtual mentoring.

Whatever the terminology, both mentors and founders can learn from how hospitasl and surgeons are participating in telementoring as an educational and research activity. Currently little research is done on the mentoring of entrepreneurs beyond a yearly customer satisfaction survey.  And founders may be even more hesitant than surgeons to participate in domain-specific educational virtual mentoring or telementoring be anxious about taking time away from running their startuip.

I will be adding “telementoring” to my Google Alerts list and studying up on how best practices in telementoring in the medical arena can be adopted or adapted for the virtual mentoring of entrepreneurs. In the field of virtual mentoring it appears that surgeons may be way ahead of entrepreneurs. Check out the article System for Telementoring with Augmented Reality and be sure to watch the video!




The pros and cons of virtual mentoring

mentor drawing

I’ve been interested in virtual mentoring for quite some time for a couple of reasons. For one, it’s the only way mentoring can scale. After all why constrain a mentor to their own locality when there are no doubt entrepreneurs across the country who could benefit from their mentoring? And, of course, it can be far more convenient for the mentor as you can  use your home office or anyplace with an internet connection. I have a Google alert for “virtual mentoring,” but it very rarely generates any results. However, today I found an article on virtual mentoring from the Harvard Business Review, an excellent source of the latest in business ideas and strategy.

While the focus of the article is on professional development for employees, as most mentoring is, there are still some points relevant to the mentoring of entrepreneurs.

The principle finding from the authors’ study conducted on employees of HCL Technologies was that mentors from varying domains can be of great benefit. HCL is a leading IT and software development outsourcing company based in India. HCL has over 103,000 employees, who are distributed globally across the firm’s own delivery centers and client sites.

Professors Bala Iyer and Wendy Murphy surveyed 1,200 HCL employees and analyzed their social networks and demographic data. They found that HCL’s knowledge management and collaboration tools improved individual productivity.

We found that employees who were connected to others via the KM and collaboration systems felt more highly engaged and productive than those who were not so well connected to mentors and were not active participants in the knowledge communities nurtured by the systems.

They found that the key to making productive use of mentors is asking interesting questions. And as is usual in business, reciprocity or paying it forward is a best practice: But be a good Netizen and remember to reciprocate: Answer others’ questions in a timely and helpful manner. 

While the HBS professors’ definition of mentor is much looser than mine – it seems to encompass anyone with domain knowledge to share – they do consider this to be the age of virtual mentors.

So why does one of the top mentoring organizations in the world – MITs’ Venture Mentoring Service – focus solely on face-to-face mentoring? Mainly because f2f is the highest bandwidth communication channel there is. In addition, by limiting mentors to MIT’s geographic area mentors can offer valuable local connections and even potential investors.  Another reason is that VMS uses a team mentoring approach. What I’ve found from the small number of virtual mentoring sessions I’ve conducted for the MIT Sandbox is that video conferencing works well for a one-on-one mentoring session, or even for one mentor to two founders. But the technology just isn’t suited for the multitude of interactions stemming from having a team of mentors interacting with a founding team. The non-verbal cues about when to speak and when to listen can get lost in a video session.

But non-verbal communication isn’t limited to knowing when to chime in. I find that if a founder is leaning back in their chair they probably aren’t nearly as engaged as when they lean in across the table. In fact, I’ve seen founders go from a lean back, disengaged posture to leaning in and eyes lighting up when I hit on a topic that resonated with them.

It’s also useful to observe the behavior of the other team members when one of them is talking. Are they all listening intently or staring at their phones? And while video conferencing apps like Zoom make it easy to view a presentation during a remote mentoring session doing so cuts into your view of the founding team.

So here are the takeaways on virtual mentoring:

  • It can enable founders to find mentors with expertise in different domains
  • It can be more convenient not just for mentors but for mentees as well
  • VM is not well suited to team or group mentoring – the aperture is too small
  • VM can be very useful in a large corporation, enabling staff to tap into expertise across the enterprise as well as outside it
  • VM can bring get staff into the habit of searching out and finding outside expertise which can be shared with their colleagues

So my search for instances of virtual mentoring of entrepreneurs will continue, but in the meantime there are lessons to be learned from mentoring that takes place in a large company like HCL. Perhaps I’ll contact the two authors of the HBS Review and try to convince them to study virtual mentoring of entrepreneurs.

Finally, perhaps I’m overly sensitive, but I find the authors’ illustration of a mentor to be less than flattering. This guy looks like a hermit who has just emerged from his cave. And he’s not looking happy about it!




Now we vibe!


Martha Sloan Felch (left) and Nurys Camargo discussed the Chica Project. (David L. Ryan/Globe Staff)

My experience mentoring non-profits has been helping founders develop and review their slide presentations at the Social Innovation Forum. SIF creates positive social change in greater Boston by engaging leaders, strengthening organizations, and building networks. I was surprised to learn that mentoring is nothing new to non-profits, according to the article Older execs turn gurus to boost nonprofit missions, sub-titled For mentors, coaching work is energizing. I can vouch for that sub-title, as I definitely find mentoring energizing. And I’m certainly an older exec, though involuntarily retired. But there is an important difference between coaching and mentoring.

Mentoring non-profits has a long history. As Boston Globe reporter Robert Weisman writes:

The mentoring movement dates back at least four decades. A group of prominent captains of commerce, led by banker David Rockefeller Sr., founded the Executive Service Corps in 1977 to strengthen nonprofits. In more recent years, as large numbers of baby boomers began leaving the workforce, dozens of other groups have sprung up, including many professional and business school alumni associations, to work with younger leaders in a range of fields. From coast to coast, thousands of seasoned mentors are seeking to impart wisdom and expertise.

Empower Success Corps deploys a network of 170 consultants to help nonprofits across New England develop and refine strategic plans. Empower charges a modest fee for its services. I’m surprised that ESC charges anything – it’s the first mentoring organization I’ve found that charges fees for its services. To me the major difference between mentoring and advising or consulting is that mentoring is always free while advisors and consultants, like other professional service providers such as lawyers and tax accountants, always charge for their services. (ESC of Northern New England (ESC NNE) and Empower Success Corps, headquartered in Boston, have recently joined forces).

Mr. Weisman captures what mentors provide to entrepreneurs and what motivates mentors:

For high-octane professionals, mentoring social entrepreneurs — as paid consultants or as volunteers — offers the chance to share skills and insights gained in the corporate world with idealistic up-and-comers who need business savvy to carry out their missions

“You’re putting people with experience together with people who can learn from that experience to deliver on their missions,’’ said Doug Dickson, board chairman at Encore Boston Network, a group that helps place older businesspeople and professionals in new roles in the nonprofit sector, public agencies, and mission-driven businesses.

For the mentors and consultants, there’s also a strong desire to contribute. Some of them lost jobs in corporate downsizing moves or felt passed over by younger executives in the latter years of their careers. “It gives them a way to continue creating value in a society that doesn’t have a place for these people,’’ Dickson said.

Others simply decided they were at a time in their lives when they wanted to give back.

I was pleased to see that Ulea Grace Lago, Empower’s director of consulting, sees mentoring as a two-way street, which jibes with my experience at the MIT Venture Mentoring Service. I feel that I learn as much from the team mentoring experience of VMS as our entrepreneurs do.

Please read the full article, which tells the story of how Empower helps a non-profit organization, in this case the Chica Project, which started seven years ago to mentor young Latinas. If you aren’t familiar with mentoring this article will help  you get up to speed.

And you too can have the opportunity to vibe with young entrepreneurs, if you volunteer to mentor at Empower or other organizations, such the Small Business Association, which works with a number of local partners to counsel, mentor, and train small businesses.




“Mentor” now chasing “Innovative” as most used and misused business term



I was dismayed by the use of the word “mentor”  in the Business Insider article by Rosalie Chan Larry Ellison says that Oracle was once a week away from not being able to pay employees — here’s the lesson he learned from the experience.

Ellison hosts a cocktail reception to mentor startup founders each year. Last week, he hosted the founders of 22 startups at his San Francisco home — and eWeek was in attendance to report on the advice he gave.

First of all it is impossible to mentor 22 people at once! Second and perhaps less obviously, mentoring is not a one-time thing, it’s relationship between the founder and the mentor that can last months or even years. Larry may well be advising 22 startup founders and perhaps he mentors a handful of them – the article doesn’t say. But mentor is starting to get overused just as the words innovate and innovation have before it. This blog devotes an entire category to mentoring.

However, the article does include two good lessons learned by Larry Ellison when Oracle was a startup, not the behemoth it is today, 40 years later.

First, is to balance doing whatever it takes to pay the bills with whatever it is that you actually want to do. One of my newest mentees is struggling over earning money from a first client, but a client that’s a real outlier on the distribution of target clients. The number one need in all startup is cash. Even if you are sharing an apartment with six other engineers and living on ramen noodles you still need cash. So I totally agree with Larry’s advice – do whatever you need to do to earn cash even if it’s NRE – non-recurring engineering. 

Second, once your startup crosses the chasm and becomes an on-going concern you can’t get complacent. As Ellison says:

The old solution to customers’ problems may no longer be the best solution. When you see that, it’s an opportunity—or a threat,” Ellison said, according to eWeek. “It’s our job as founders and developers to constantly change our companies based on technology available today that wasn’t available yesterday.

And like every other company, Oracle is realizing that AI is not just a science experiment any longer, Oracle has been focusing on its autonomous, AI-powered database and its cloud solution.

As a mentor I hope that the it remains a term of art, unlike innovative, too often used and misused as in “new, innovative” which is redundant, as the very definition of innovate includes the word new.

innovative |ˈinəˌvādiv| adjective(of a product, idea, etc.) featuring new methods; advanced and originalinnovative designs | innovative ways to help unemployed people.(of a person) introducing new ideas; original and creative in thinking: an innovative thinker.

Well I’ve hit my pedantry quota for the day!



Why everyone needs a sounding board!

sound board

If you aren’t familiar with the term sounding board here’s the dictionary definition:

2. a person or group whose reactions to suggested ideas are used as a test of their validity or likely success before they are made public: I considered him mainly as a sounding board for my impressions.a channel through which ideas are disseminated.

Ever since my very first startup, providing sound reinforcement services for local bands, my wife has served as my principle sounding board. What I’ve learned over the years is that having a sounding board is very important to founders for several reasons:

  • Running your ideas by your sounding board forces you to work on articulating those ideas clearly and concisely.
  • If you have a non-technical partner like my wife, you will be forced to put your startup ideas into a format that any intelligent, but non-technical, person can understand – a good thing!
  • My father always used to say You don’t really understand something unless you can explain it to someone else. I’ve found that to be true!
  • Sounding boards are a facet of mentoring and mentors do act as sounding boards, but a sounding board is a much more lightweight role, as experience and knowledge of the startup world aren’t required.
  • My  wife is a great editor so often I would run documents like an executive summary of my startup business plan by her – sounding boards don’t always rely on sound!
  • You do have to be careful in choosing a sounding board, as family and friends can easily tell you want they think you want to hear, which is worse than not helpful, as it can let you go off in the wrong direction. Skepticism is a baseline requirement for sounding boards.
  • Acting as a sounding board for others can help you hone in on what you need as a sounding board for your own ideas.
  • Too many sounding boards can end up creating confusion, like the old saw Too many cooks spoil the soup.
  • Don’t  wear out your welcome. Use your sounding board sparingly, if you need deep and frequent feedback seek a mentor.
  • At the end of the day you own the decision or the work you’ve asked your sounding board to  weigh in on. Under no circumstances should you criticize your sounding board for the feedback they gave you.
  • Finally, I’ve used this quote before, but it applies directly to sounding boards: Perspective is worth 80 IQ points, according to computer scientist Alan Kay.

If you have mentors that’s great, a sounding board can be another source of feedback for you. But if you don’t have a mentor, a sounding board becomes more important and may be a first step for you on your way to engaging in a mentoring relationship.

According to the dictionary defintion sounding board is another term for soundboard, which I found amusing as when I worked in the sound reinforcement business that’s what we called our mixing desk. But feedback – of the screeching audio variety – was most definitely not that we wanted from our soundboard!


Prescriptive vs. Socratic mentoring

decison 2

Over my ten years of mentoring at MIT and elsewhere I’ve worked with a large number of other mentors, as both the MIT Venture Mentoring Service and the MIT Sandbox Fund employ team mentoring. Teams can range from two to as many as five or six.

Every mentor has a different mix of experience and expertise. What we all have in common is that we have been screened by the VMS or Sandbox management and we all agree to adhere to the code of ethics.

What I’ve observed is that there are two basic modes or styles of mentoring: prescriptive and Socratic. The prescriptive mentors tell the founders what they should do – their mode is instructive or didactic. Their advice is usually clear, concise, and quite directive. Socratic mentors, such as myself, ask questions, which we believe will lead the founder to examine his or her options and the pros and cons of each. We focus on decision support, not making decisions for the founder.

Both VMS and Sandbox have very short time horizons: mentors focus on what founders need to accomplish in the next month or two, not the next year or two. Advice is usually quite concrete, not abstract, and next meetings are predicated on achieving agreed upon milestones.

No mentor is 100% prescriptive nor 100% Socratic. Occasionally I will be quite directive if I believe the founder needs to do something or they may suffer negative consequences. Often these situations are legal issues, such as trademark, copyright or related intellectual property matters. My advice is these cases is “Book time with the VMS legal mentor or BU Law Clinic ASAP!” Conversely even the most prescriptive of mentors will ask a clarifying question or two before instructing the founder on a course of action.

What can be challenging is when you have only two mentors on a team and one is directive and the other non-directive. The poor founder’s head is on a swivel and I can see confusion set in. At such times I’ll try to reframe the prescriptive mentor’s directive into a question to give the founder a chance to reflect and think about the advice being given.

Mentors provide advice, guidance, feedback, perspective, and support. My goal is to help founders succeed in pursuing their goals. But it often takes a number of questions to actually find out what those goals are! Reviews and feedback on a presentation is perhaps the simplest mentoring exercise, while providing advice to a founder having problems with a colleague is the most difficult. But my interim goal in helping a founder to succeed is to get them to think. And to think about their options, the pros and cons of each and most importantly, the repercussions of following one option versus another.

Founders tend to have a bias for action, but sometimes the most important advice I can provide is, “What a minute!” Usually followed up with a question, such as, “Have you thought about X?”

If you are a founder in a mentoring relationship it would serve you well to learn to recognize these two modes of mentoring. You can respond to the highly prescriptive mentor with your own questions, such as “Why are you recommending that course of action?” “What are my other options?” “How do they compare with your choice?” Conversely when you find yourself subject to a series of questions from a Socratic mentor you might ask them to pause and say something like, “What would you do if you were in my place?” “I need to make a decision now, can you give me more specific advice?”

Of course, the most important mentoring skill is neither asking the right question at the right time nor recommending a single course of action you deem best. It is listening. And listening needs to be active, not passive. Active listening is comprised of four elements:

  1. Concentrating fully on the the listener – don’t start thinking about your response while your founder is still talking! Pay attention to body language. Are they leaning forward or backward? Looking relaxed or tense? Speaking rapidly, softly, or loudly?
  2. Understanding – don’t assume you understand. Check with the founder. Ask him or her directly, “Is this what you mean?” or “Could you clarify or amplify that?” or “Here’s what I hear you saying, am I correct?”
  3. Responding – the key is that your response be relevant and helpful. Be concise. The best advice is actionable, as founders are always under pressure to decide their next step.
  4. Remembering – if need be take notes, but make sure you keep track of what has been said, how you responded, and if the discussion seemed to help the founder or not.

While having an undergraduate degree in psychology is mildly helpful to me, I wish I had taken a course or two in counseling, negotiation or conflict resolution.  However, most mentors have learned our skills from our own mentors or observed other mentors in action. Given the prevalence and importance of mentoring I would like to see a course dedicated to the best practices in mentoring entrepreneurs.

In the meantime, mentors should be aware of their style and consider modifying it when appropriate. And that’s about as directive as I’ll get!


Why mechanized mentorship won’t work


My Google alert for “mentorship” provided an interesting result the other day: So what is According to their home page:

thirty2give is a smartphone app that facilitates formal and informal pairing of mentors and mentees anywhere in the world. thirty2give’s new smartphone mentoring tool is now available for iPhones at the Apple App store and Android phones through Google Play.  It solves the growing math problem of matching mentors and mentees around the world.  We believe that great mentors are great because of their degrees, they are great because of their experiences.

Thirty2Give joins LiinkedIn and Facebook, both of whom announced their own peer mentoring services recently. From where I sit this is not a good trend. Why? Because not everyone is suited to be a mentor. The best way to find a mentor is to work with a mature organization that is experienced in vetting and onboarding mentors. The MIT Venture Mentoring Service has been perfecting its mentoring model for about 18 years. Mentors must be recommended by fellow mentors and then are interviewed extensively by the VMS staff. From my own experience I can tell you that not all nominees are invited to mentor, I’ve had two rejected to go with the two who were accepted.

VMS trains other organizations in its mentor model and to date there are about 75 sister programs around the world. Local accelerators and incubators also offer their ventures access to a mentor pool. I’ve written several posts about finding a mentor and mentor-founder fit. I won’t reiterate them here, but the key point is that mentors need to be qualified by an organization with bona fides in the entrepreneurial ecosphere. Simply mechanistically or algorithmically connecting wannabee mentors with wannabee mentees is a recipe for failure. It takes a thoughtful, careful, experienced, and in-person process that can’t be reduced it to an app. While many matches, like drivers and ride hailers, can be matched by a machine, these tend to be transactional, not consultative relationships like mentorship.

Thirty2Give’s customer base seems to be just about everyone: Anyone with a smartphone can find a mentor anywhere based on their specific need. This is a serious mistakeOrganizations providing mentors need not only expertise in recruiting, training, and retaining mentors, they need domain-specific experience. The two most common domains for mentorship are entrepreneurial and career-driven.

But that’s not the worst of this model: the press release that Google Alerts found is headlined: Thirty2give Announces B2B Version of Mobile Virtual Mentoring App. While I have a deep interest in virtual mentoring, it is actually just a mentoring mode. Face-to-face is the highest bandwidth mode of communications between mentors and mentees and for that reason MIT VMS relies on it exclusively. However, MIT Sandbox, where I also mentor serves students, many of whom work from home during the summer and breaks. But MIT, being a highly international institute, many of those homes are outside the U.S. For that reason I’ve been using Skype to mentor several Sandbox ventures. But like VMS, Sandbox is a non-profit, academic service organization serving students and headed by an executive director with a lifetime of experience at MIT as an undergrad, PhD., and Housemaster. I can’t imagine a better executive director than Jinane Abounadi.

My advice to anyone seeking a mentor is to perform careful due diligence on the sponsoring organization. Are they for profit or non-profit? What is their experience in providing mentors? How do they qualify mentors? What is the background – experience and expertise – they require of their mentors? What is their reputation is in the entrepreneurial community? And what do they expect of you, the mentee?

I’ve found that virtual mentoring can work given a strong parent organization and a very tight agenda and set of objectives for a virtual mentoring session. In fact virtual sessions tend to be more time efficient as the small talk and socializing that often takes place in face-to-face mentoring sessions is not so easy over a video connection. And not all video communication tools are best suited for mentoring. More about virtual mentoring in future posts, but for now a word of warning to would-be mentees: be highly selective about where you get your mentoring from. Act as if you were applying to an educational institution, because in fact mentoring is an educational function. The MIT Venture Mentoring Service reports directly to MIT’s Provost. Just because an organization like Facebook, LinkedIn or Thirty2Give can connect you with a would-be mentor does not mean that they should! Nor do you have any assurance that would-be mentor is a good fit for you and your venture.



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