Benefits of mentoring – a woman’s perspective



Let’s face it, guys, tech is overwhelming male, from the boards of directors to the senior executives to the staff. And including mentoring groups. This issue has gotten a lot of press lately, so no reason to reiterate the issue. But I thought Rebecca Shireman‘s article in Florida Today Mentoring benefits all who are involved was well worth posting about for two reasons: one, it’s a well written article that does a great job of articulating the do’s and don’ts of mentoring, and two, unlike most of the posts and articles I comment on and annotate, it’s written by a woman, not a man. As Alan Kay said, “Perspective is worth 80 IQ points”. So here’s a woman’s perspective on mentoring. As usual, I will follow the steps outlined in her article, but annotate each of them with my own comments. So read the original article, please.

For a long time I thought I didn’t have a mentor –I’d never asked anyone to be my mentor so how could this relationship have been established? Yes, I had women (and men) that I looked up to and who gave me their valuable insight and advice but since we didn’t meet once a month and I had never made the formal request, I didn’t think this really “counted” as a mentor. Then I read Sheryl Sandberg’s book and I realized in the case of finding a mentor that it is okay to break the “rules.”

 Ask for a meeting, not a mentor. My first rule of business development and sales is “get the meeting.” So while getting a mentor is neither activity, the rule still applies. Nothing is better than a face to face meeting. And nothing is better than a conversation. Mentoring is a relationship that needs to develop, like a friendship. You can’t just jump into it with a total stranger and expect it to work.

 Show genuine interest and curiosity. If you aren’t genuinely interested in the mentor, he or she will pick up on that very quickly, trust me. I’ve seen a couple of cases where founders had to participate in mentoring in order to qualify for a grant and obviously weren’t happy to be there. Mentors are curious people and expect founders to be as well.

 Be respectful of his or her time. A very large percentage of mentors are financially secure, but no matter how much money you have, you only get 24 hours in a day. Time is a mentor’s most valuable resource. Again, one of my business development principles applies, get there early – not just “on time.” And nothing shows more disrespect to a mentor than being late for a meeting! And end the meeting bit early too, if the mentor wants to talk further let him or her pull you back.

 Don’t make it all about you. Mentors are like founders, they like to learn. It’s a real benefit of mentoring bright, dynamic young entrepreneurs. So learn your mentor’s interests and be on the look out for news or information that might interest them. And keep in mind, you don’t learn anything while you are talking, only when you are listening. So come prepared with a good list of questions to address in your mentor meeting.

 Manage expectations. Look to mentors for advice, guidance and feedback – not miracles! One expectation to set is how often you will meet and for how long. Too frequently, such a once a week is too often. But leaving months between meetings isn’t good either. Ask for a meeting when you have something important you need help with. It’s fine to cancel a meeting – with enough notice – if you don’t need help at that appointed time.

 Initiate but don’t be a pest. There’s a fine line between being assertive and becoming annoying. Keep in mind bullet number three – respect your mentor’s time. That includes time reading and responding to your emails, not just meeting with you.

 Be a mentor. You don’t have to wait until you’ve hit the jackpot, cashed out and retired to become a mentor. Peer-to-peer mentoring is an interesting option and one that is encouraged in accelerator and incubator programs like Y-Combinator. Mentoring is stimulating, fun, and can be a challenge. It’s also rewarding to see how your mentoring has helped the founder to hit a milestone, solve a problem, or come up with a creative approach to their business.

Great article about Paul English on mentoring and being mentored


CREDIT: Getty Images

Paul English co-founded Kayak, which he took public and then sold to Priceline for $2 billion in 2013. We pitched Paul on Endorfyn, the PopSleuth app that alerted fans to new content from and about their favorite artists. He didn’t have any interest in investing, but he had some good feedback on our UI and our strategy. What was fun about the meeting was that in addition to meeting Paul we also met Tracy Kidder, who was then shadowing Paul for his book A Truck Full of Money, about Paul’s entrepreneurial career.

In the Inc article I Have Never Met A $1.8 Billion Founder Like Paul English by Peter Cohan Paul talks about both mentoring and being mentored. Here are some excerpts.

 … the thing that makes English unique is his passion for helping other people through mentoring.

And just as he now mentors younger entrepreneurs, he found himself in search of mentorship when he started founding companies. “Earlier in my career I would look for someone who was not my boss — maybe my boss’s boss or a peer or someone outside the company. Scott Cook, who cofounded Intuit, continues to be my mentor,” said English.

He gave me several examples of how mentoring helped him be a better manager. “Mentors helped me understand that when working with a cofounder, it is better to split a startup’s equity 50/50 because when things get challenging you will both be highly motivated to find a solution.

Finally, mentors helped me appreciate how important it is to seize every customer interaction as a learning opportunity

Paul introduced author Peter Cohan to four people who talked with him about mentoring.

Vinayak Ranade English mentored Ranade through his example and coaching — teaching him the importance of hiring the best team.

Sara Wood, He gave me advice on scaling companies; the legal obligations of an executive; and how to read the capitalization tables in a Series F fund raising to ask tighter questions. He’s helped me raise money by serving as a reference for investors conducting due diligence. And he’s helped me to give better performance reviews to build trust on both sides.He also taught me the importance of thinking and being like the customer.”

Polina Raygorodskaya,  Paul helped me to understand why branding was important and how Kayak built its brand. He also introduced me to his VP of Engineering to find out how they integrated with their partners.”

David Cancel Mentoring is a way for humans to simulate how they might act by using other people’s 10, 20 or 30 years of experience to model where the might want to be in the future. Paul helped me to learn the importance of people — particularly recruiting experienced people in areas like sales leadership and finance. By taking a long view of how I can help them achieve their career goals, I have gotten better at overcoming the challenges of hiring such people.”

I love David Cancel’s quote about mentoring as a simulation! I’ve never heard anyone express mentoring in that fashion and it’s a great way to think about it.

Paul English sets a great example for other CEOs who “have made it” by paying back through his mentoring of other entrepreneurs. And, from the examples given by the four founders, his advice is gold plated. Not exactly, a truck full of money, but perhaps by following it you will get your own truck full, or at least a wheel barrow’s worth.

A step-by-step guide to finding and working with a mentor

women mentors

Shana Hocking‘s Forbes article How to Cultivate Great Mentor Relationships and Grow Your Career, while focused on career mentoring, is quite applicable to the mentoring of founders as well.

As usual in annotating articles of this type, I’ll keep the outline of steps recommended but add my comments to each step. So make sure to read the original article if this subject is of interest to you.

What are you looking for from a mentor?

We need to manage expectations here. Mentors are generally ok with giving advice, feedback and guidance based on their experience and expertise. Thus mentors make great sounding boards – but it’s up the mentee to make the sounds. Where mentors may differ is in the willingness or ability to make connections. As I was told by one mentor when asking for a connection to a well-known founder “Keep in mind I have only so many arrows in my quiver.” Mentors want to be sure there is something in it for their connection as well as for the mentee. Another subject you need to clarify with any mentor is their interest in helping you with fundraising. On the rare occasions when I am mentoring a startup that is fund-raising ready – team, prototype, customer traction – intersects with the funding interests of a VC I know I will reach out to make an introduction.

Identifying a mentor

If you are fortunate enough to be affiliated with an institution like MIT there are multiple programs that also offer mentoring. If you only want mentoring you would choose the Venture Mentoring Service, but if you are looking for a financial grant, you would try The MIT Sandbox Fund, which also provides mentoring. But if your college or university doesn’t offer mentoring to its alumni you will need search your network, and spend a lot of time at networking events. But first know what you are looking for. The most important discriminator is do you need domain expertise or not. What I find is that most early stage startups have similar business issues and a generalist like myself can usually be helpful. But once a venture gets traction it’ need for advice and feedback often gets specific to it’s market. So that’s why I never volunteer for medical device or bio-engineering mentoring engagements – I have less than zero knowledge of those fields. Be sure to ask your colleagues and fellow founders if they have a mentor or mentors and how they found them.

Asking for the meeting

As with investors, warm introductions are by far the best. Cold contacting a mentor may waste your time unless you have some strong common ground, such as both graduating from the same school and majoring in the same subject while working in the same market. But the most important thing to have when asking for the meeting is to offer something of interest to the mentor. Be sure to read my post How to get meetings with people too busy to see you: do your homework! Any good mentor is going to be busy and in demand. But all good mentors are curious people, so have something that piques their curiosity. Not what makes you new, but what makes you different and interesting.

Cultivating an excellent mentoring relationship

Establish guidelines with your mentor

This is an easy one, as established mentors will have established guidelines. So it’s up to you to make sure you understand those guidelines – such as “I can only meet at night or on weekends” and abide by them.

Prepare for your mentoring sessions

This is an important step and one that I don’t always see in articles like this one. Prepare an agenda in advance and email it to your mentor. Make sure you know in your own mind what questions you need answers to or what decisions or activities you are looking for feedback on.

Add value to your mentoring relationship

This is important! While many of us mentor to “pay it forward” or “give back” mentors like myself also like to learn something as well. Here’s I’ll directly quote Shana Hocking’s solid advice:

Mentoring is a partnership and mentors can get as much from the relationship as they give. Is there a skill you can teach, generational insights you can share or industry perspective you can bring? Oftentimes mentors find the most joy in just being a part of your professional development.

Keep in contact with mentors

One of my frustrations with mentoring is when I give advice or offer feedback on an upcoming event, such as an investor meeting or demo day, and don’t hear back on how it went. Don’t do this to your mentors! We are invested in your success! Make sure you don’t just contact your mentors when you need help, we like hearing success stories as well.

Consider peer mentoring

Again, this is something most authors who write about mentoring don’t cover. I was flattered to have one of my fellow mentors ask me to mentor him. We’d participated in a few mentoring sessions together – MIT’s VMS features team mentoring – so we knew each other a bit. If you don’t read any other part of the article read this section and keep it in mind, especially if you are having trouble finding a seasoned entrepreneur as a mentor.



If you’re a sport fan of any sport, chances are very good you are familiar with the term MVP and what those initials stand for: Most Valuable Player. But if you frequent the entrepreneurial ecological system of founders, VCs, angels, lawyers, accountants, consultants, and mentors the chances are that your first reaction to the term MVP is Minimum Viable Product.

A minimum viable product has just those core features sufficient to deploy the product, and no more. Developers typically deploy the product to a subset of possible customers—such as early adopters thought to be more forgiving, more likely to give feedback, and able to grasp a product vision from an early prototype or marketing information.

The MVP emerged from the lean startup model polemicized by Eric Ries

And I have to say, that until recently I bought into the MVP concept myself. However, a few weeks ago I came across a post somewhere – and Google can’t seem to help me retrieve it – that made a compelling case that you don’t want to create an MVP – a Minimal Viable Product, but an MRP, a Minimal Remarkable Product. The case was made that simply putting out a product that is just capable of working successfully with a small set of features,  but no more, is not going to get your customers’ attention. And we are in a battle for attention. “It’s the attention economy, stupid.” Which I have posted about previously.

So while it might make sense for developers to develop MVPs, marketers should demand MRPs – products that get customers’ attention.

So rather than putting out a product that just barely meets the standards of viability on a minimum set of features, focus on what it is that makes your product … remarkable. What is that differentiates your product or service from your competitors, but equally important is attention-grabbing enough to compete against the literally millions of other products and services seeking to grab your customers’ attention? Build that feature up past minimal to captivating, while following the rest of the MVP playbook for the rest of the product. Then lead your demos with that feature and equally importantly, explain how that feature delivers the absolutely must-have benefit that your customers will crave.

In searching for the original post on the MRP I came across this good writeup on Medium from someone who had participated in Y-Combinator’s Startup School. Here’s the quote from Aly Juma’s post 10 Lessons I Learned From YCombinator’s Startup School:

Build your Minimium Remarkable Product (MRP) fast.

We’ve heard a lot about minimum viable products over the years, but a new terms I found from YC is the idea of the minimum remarkable product.

The point is not to be viable because that means self-sufficient, you waited too long. What you want initially is to be remarkable. You want a single feature or thing about the product that at least one person see’s real value in. Then you grow from there.

Some day I hope to find that original post that caught my attention but which I failed to record. Then I’ll update this post. But that’s probably of interest to a few. The concept of Minimal Remarkable Product should be of compelling interest to everyone in the entrepreneurial world.

Getting big fast – but how fast is fast?

matthew prince

Matthew Prince, chief executive of Cloudflare, says that adding more employees too quickly can erode the foundations of company culture.CreditEarl Wilson/The New York Times

The mantra of the first .com bubble was “Get big fast”: collect as many eyeballs as possible and then figure out your business model later or sometimes never.

This idea worked enough times – Google, Facebook et al – that VCs made it their deal selection criteria: how fast could a company get big?

As I preach to my founders, VC capital is rocket fuel: you need it for escape velocity. But like rocket fuel, it’s the most expensive fuel you can buy.  And getting big fast can lead to some real growth pains, witness Uber.

So where the sweet spot in the growth curve? Matthew Prine CEOf of Cloudfare, a cybersecurity firm has a simple and compelling formula that is well worth emulating.

Matthew Prince is  interviewed by Adam Bryan in Corner Office in this New Your Times article. Note well the title of the interview: Matthew Prince of Cloudflare on the Dangers of Fast Growth.

Prince saw the problems of high growth before he started growing his company:

I also watched other companies stumble because they grow too fast. If you’re growing faster than doubling the number of employees in any 12-month period, then inherently you’re going to have more new people than old people. And in the short term, maybe that’s fine. But the culture can start to suffer because there’s nothing foundational to keep you stable.

As I’ve written elsewhere, culture is the foundation of any startup and as Prince points out, growing too fast can destabilize your foundation. So unlike any other founder I’ve come across he’s developed a formula for both the company and teams to guide the company’s growth:

We have a rule across the organization, and on a team level, to never grow faster than doubling in any 12-month period. For start-ups like us, there’s constant pressure to grow faster, but if you do that, then there are no culture-keepers of the organization.

Adam Bryant, who is one of my favorite writers about tech, always asks the question in his Corner Office interviews “How do you hire?” While this doesn’t seem to relate directly to how fast you grow, it actually does.

I look for an incredibly high degree of curiosity — people who just relentlessly want to learn new things and put themselves in new situations — and a high degree of empathy. If people are curious and empathetic, they can learn just about anything.

As I’ve written previously companies stay competitive by learning faster and better than their competitive and applying what they’ve learned. So concentrating on the quality of your hiring is more important than quantity. Rather than “Get big fast” consider “Get smarter faster.”

I can’t resist one more quote from Matthew Prince, because it’s something I’ve been doing every since becoming a hiring manager decades ago and I’ve found it very effective, just as he has:

One of the best ways to tell whether someone’s curious and empathetic is to ask them for the questions they have. You can see how their mind works and how thoughtful they are.

So yes, once you have nailed your business model it’s time to light the rocket and take off. But be careful, many launches blow up on the launch pad due to poor preparation for launch. Following Prince’s growth formula and hiring staff who are driven to learn new things will prepare your venture for a successful lift off.

Business megatrends can lift all boats



It’s a dirty little secret that investors – and veteran entrepreneurs as well – look to build companies on the back of a business megatrend. This strategy is based on the truism that “a rising tide lifts all boats.”

But what is a business megatrend and how do you know you have found it? First of all it’s not a technology megatrend, like AI which plateaued for  decades until finally the intersection of rising computer power and the dropping price of data acquisiton and storage enabled it to finally take off. Business megatrends affect customer buying behavior and supplier selling behavior. You don’t have to be a technologist to understand a business megaTrend. But if you are a technologist who ignores a business megatrend your venture is missing out on the opportunity to draft behind very powerful forces.


Self-service was the business megatrend of the last century. Whether it was ATMs or self-checkout at supermarkets, this megatrend caught on for the simple reason that it benefits  both two sides of the business equation: supply and demand. From the suppliers’ viewpoint self-service cut costs. Why pay a teller when you could replace one with a machine that never took sick days or vacation days and didn’t mind standing in a cold vestibule or even outside! ATMs, like many tech advances, follow the hockey stick curve, very, very slow growth followed by an inflection point where they take off and become ubiquitous.  From the demand side, otherwise known as the customer, self-service saved time, which has become the most valuable commodity of the past and this century. Why stand in line when you could just scan your items yourself at your super market and check out yourself? Fast and equally importantly, simple and easy. The key with megatrends is that they always have secondary characteristics that make them very attractive to one or both sides of the business equation.

While many businesses initially worried that self-checkout would result in customer theft what they found instead was that it cut down on employee theft (and errors).

So today we just take self-service for granted as it spreads from airline ticketing kiosks to smartphone payment systems. Fast, easy, simple for the customer; saves costs, collects data, and reduces losses for the business.


Personalization has superseded (NOT replaced) self-service as the megatrend for the 21st century. Burger King encapsulated this trend with the ad slogan “Have it your way!” The beauty of mass production for the supply side was economies of scale, from the supply chain to the manufacturing floor to the retail store. Mass production greatly benefited the supply side by cutting costs, helping to ensure quality and cutting down on returns and customer complaints. But the prmiary characteristic driving personalization is novelty. Customers seek novelty – they always have. Otherwise teenage men could have done just as well with just a single copy of Playboy rather than a subscription. “New” is probably the second most used and powerful sales term after “Free”. Trendsetters are on a constant prowl for what’s new. But what happens when the masses all discover what’s new? It’s no longer cool. Enter personalization. Amazon proved to be a master of self-service with it’s invention of the “one-click buy” – a business process it even succeeded in patenting. But Amazon soon discovered it could use it’s massive amounts of customer data to personalize the buying experience by providing recommendations for additional purchases – known as upselling- based on what the customer was buying. Real time personalization! While Spotify was a great success, where  it has hit its inflection point has been its successful implementation of personal playlists for its customers. So just as fast and easy is the secret sauce of self-service, finding what’s new is the secret sauce of personalization. And what could be better than “what’s new FOR YOU?” Talk about reducing returns and customer complaints, personalization greatly benefits the supply side. With AI finally coming out of its doldrums, coupled with big data, businesses will be able to harness the power to personalize more and more of the customer experience, because it is based on the customer’s own behavioral data. Google now uses its knowledge of your prior searches to personalize your new searches. Soon AI-based systems will achieve the ultimate in personalization: they will know what you want before you do!

The bottom line

While there are many reasons for the amazing success of Amazon, you don’t have to look to far beyond the two megatrends of self-service and personalization, which Jeff Bezos harnessed so brilliantly to achieve his relentless focus on the customer.

So if you are doing a startup today, take a step back. Does your venture take advantage of the power of self-service by saving the customer valuable time? Is it simple, easy and quick to use? Does your product or service utilize customer data to personalize the product or service so each customer gets their personal and optimal buying experience?

What will be the next business megatrend?

It may well be the demise of cash and credit cards – supplanted by Bitcoin or its cousins. But while you may win big betting on the next megatrend will be, the safe and sound way to go is to capitalize on the proven megatrends of today and yesterday: self-service and personalization. There are still billion dollar businesses to be built on top of these two megatrends.


The best way to increase your startup’s chance of success



The Forbes article How Startups Can Find the Yoda of Mentors by Meghan Larson, founder of Adistry, is a very good, short introduction to the value of mentoring to a startup.

There is a simple strategy that typically gets overlooked that can increase your startup’s chances of success more than anything else: working with a mentor.

The article outlines four steps to finding a mentor. I’ll list them, with my comments attached, As always, read the original article for the author’s viewpoint.

  1. Think about what you need help with the most. While it’s ideal to find a mentor with domain expertise in your market and experience working in that market, it’s not a requirement. Mentors don’t have infinite time to spend with you, so think carefully about what issues you need help with? Creating the right company culture? Organizational design? Feedback on your investor pitch deck? A truly experienced mentor who has succeeded in business will be able to help you regardless of what industry they gained their success in.
  2. Establish a mutually beneficial relationship. . Unlike executive coaches, mentors do not charge for their services. Mentors are thus fully aligned with the goals of the company, unlike coaches who’s motivations may be more focused on their personal monetary gain. However, there is nothing wrong with giving a mentor shares of stock to thank them for their help. My rule of thumb was to allocate 1/2% to 1% of the company’s shares to an entire advisory board of six or seven members. Instead of a four year vesting program that is standard for employee you might want to make it one year for a mentor and look at renewing your relationship on a yearly basis.
  3. Network like a pro. The most common question from founders is, “Ok, but how do I find a mentor? The author recommends networking: “Technology meetups, hackathons and industry conferences are optimal environments for discovering your ideal mentor.” However, before that I’d recommend you try your personal network and the personal networks of your co-founders. Always better to have a warm introduction. As Meghan Larson points out, your investors have a portfolio of companies to tend to. “They excel at helping you with your next raise.” Rely on your mentor for advice, guidance, and feedback on an as-needed basis.
  4. Trust your instincts. You need the right chemistry with your mentor – it’s a relationship of trust. However you also have to protect the company. You should have a Letter of Intent with your mentor that spells out what they will do for you and how many shares you will grant them under what T’s and C’s. And of course, mentors need to sign NDAs, as they will be privileged to confidential information about the company. Meghan has a great tip on this LOI: “A great advisor will suggest improvements to your agreements before signing.”

Here’s her close to the article:

Recall Yoda’s wise words when entering into a mentor-founder relationship: “You will find only what you bring in.”

While this article is a good start, there are several other articles on my blog un the Mentor category, including posts like Mentor/Founder Fit and Don’t just find a mentor. Allow yourself to be mentored.. There’s a lot to mentoring and being mentored. That’s the purpose of this blog: helping both mentors and mentees.