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Revisiting Mentorship: Diversify your Mentors as you Grow your Startup

mentorshipIt’s a generally accepted common practice that startups benefit from mentoring, especially while in their early stages of development. There is no shortage of mentors in startup communities and mentor networks among accelerators who pride themselves on such value-added, and it is a good thing during these startup stages.

In this post, I’d like to first segment the types of potential mentors, then suggest evolutionary mentorship sources for more mature startups.

So where do mentors come from?

  • Peer entrepreneurs
  • Role models
  • Corporate employees
  • VCs
  • Angel investors
  • Board members
  • Advisors
  • Accelerators program managers
  • Expert consultants
  • Pundits
  Each one of these segments has their strengths and weaknesses. The strengths are typically obvious and they depend on how much the mentors know about your particular situations, and their own experience in the mentoring process. [The Techstars Mentor Manifesto is a good refresher.]

But their weaknesses are more invisible, and they are the kinds of things that a startup CEO needs to either discount, or be aware of.

Peer entrepreneurs may not have experienced what you are going through.

Role models sometimes have a better image than substance.

Corporate employees may be unrealistic about startup realities.

VCs will most often see things according to their own thesis and agendas, and if you are getting mentored by VCs who have invested in you, they can be too emotionally attached, and more forgiving.

Not all angel investors have had broad operational experience.

Sometimes you end-up with the wrong Board member, and that creates tension when listening to them.

The advisors you pick initially may be useful then, but if they don’t evolve with you, their value may diminish over time.

Program managers in accelerators are typically junior and don’t have depth or breadth.

Expert consultants will tilt on advising you more than mentor you.

Pundits may be more visionary, and sometimes not so relevant to your immediate priorities.

This diversity in mentorship choices is a good thing for early stage startups, but as a startup matures, I suggest they should re-think who their mentors are.

As a startup grows and finds product/market fit, there is less and less ambiguity about their business. With less ambiguity,  you need less ambiguous mentoring and support. The mad, fast and furious moments of early stages gradually becomes less mad, less furious and more measured and structured, as the startup grows. Therefore, the type of mentoring required becomes more prescriptive and less suggestive because several situations and issues will have more clarity to them.

I recently advised a startup to consider vesting an advisor package to 1-2 years, not 4 years, because you can’t really predict the value of the same advisor over 4 years. If they are great, renew them yearly.

Take a page from Brian Chesky who expanded his mentorship horizons, and went really high by picking some legendary role models and asked them for specific mentorship and learning advice. It is a bold move, and I’m not suggesting that any startup CEO could have easy access to these types of people, but the point is to aim high and try to go out-of-the-box when it comes to mentoring support.

Screen Shot 2015-08-25 at 6.30.07 PMSource: The Education of Airbnb’s Brian Chesky (Fortune).

What’s so interesting about getting advice from successful CEOs of bigger corporations or larger startups? They have honed in their execution capabilities, and know well how to manage people and objectives. And they know how to be strategic while at the same being operational, so you can learn from them how they manage that balance. Each seasoned CEO has a few unique tricks and rituals, and maybe one them will click with your needs or personality. I wrote a blog post titled Managing a Startup Isn’t Different – Don’t Re-invent Everything, because I saw first-time startup CEOs trying to reinvent management in their own ways. My suggestion is to go back to first principles of management, and read a couple of old-fashioned books on being a first time CEO, then discount what doesn’t apply, but take what applies. But don’t discount the basic principles of managing people. Or read Matt Blumberg’s Startup CEO book.

So, my advice is to think about re-evaluating your mentors, role models and advisors at every successive funding round or stage of growth that you reach.

Your needs are changing, so why not change who you are being surrounding with and influenced by?


The Biggest Blindspot of a Startup CEO is Ignoring Their Brand

Ceo leadershipI’ve been critical of startup CEO’s whose startup has traction, but they can’t seem to rise-up to make their company great by recognizing that elevating their company’s brand is their job, not the marketing department’s.

Traction, users and early revenue is a God’s gift to a startup, and it is a fuel that lets you go to the next level. How you take advantage of that is a key question.

It was heartening to read that Brian Chesky, one of my favorite startup CEO’s has 3 priorities he passionately focuses on: Product, Brand, Culture. It is no coincidence that these 3 areas represent the 3 poles of a company’s structure: its users (product), its market (brand), and its employees (culture).

Screen Shot 2015-08-17 at 12.57.33 PM

In addition to the confirmatory point that Brian Chesky is pro-active at being the bearer of the Airbnb brand, it is not a coincidence either that Airbnb’s valuation ranks as one of the highest among startups, on a per employee basis, with a respectable #4 position in private companies (behind off-the-charts Snapchat, then WeWork and Pinterest, and ahead of UBER). This confirms pretty much what I have recently written in my post, Why a Strong Brand Means Higher Growth and Better Valuation for your Startup.

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The Fortune article that chronicled The Education of Airbnb’s Brian Chesky is a fascinating read, offering an insightful roadmap and inspiration to any young startup CEO who needs to rise-up, and has a calling to become a leader. In my opinion, Brian’s self-aware roundedness is the new Tech CEO archetype, not someone who came from product management necessarily.

Brian Chesky self-educated himself at age 33, as a first-time CEO, as he became obsessed with figuring how what he needed to learn. I know that exact feeling, because at 27, when I became a young manager at HP, I started devouring every management and leadership book I could find, and got help from other more senior managers. As a manager, if you don’t obsess with mastering Management, then I’m not sure what is more important than that.

The other key thing about the Fortune article is that Brian Chesky decided to take his mentorship up, not sideways. I see a lot of emphasis in startups on peer groups for support and learnings, and although peer groups are great, you won’t learn something if your peers haven’t yet experienced it, and you certainly won’t get the depth and breadth of knowledge from more seasoned mentors. Brian Chesky went to Warren Buffett, George Tenet, Sheryl Sandberg, the CEO of Disney and Jony Ive chief design officer at Apple.

Back to Chesky’s 3 priorities (Product, Brand, Culture), it is not unusual to see Product and Culture on the list of other startup CEO’s priorities. But it is less likely to see Brand on it. “Brand” is that blindspot that many startup CEO’s have if they don’t value its importance. Brand pulls you forward and it helps you grow. It is the CEO’s responsibility to be the brand ambassador. If they can’t, they have a problem. It is not just up to the marketing department. At some point in time, when your product/market fit is helping you grow, it is time to Focus Your Startup Marketing on the Mind, not the Product.

To all tech startup CEOs, my archetype is Brian Chesky. I previously lauded Airbnb for consciously working on their brand as they positioned themselves to be in the Hospitality business, and not in the spare room or sleeping-on-the-couch service. I am now impressed to see how Brian Chesky has become an original, self-taught, rounded leader that values the importance of his brand.

I will end this post with my favorite Brian Chesky quote from that Fortune article:

“Usually in a crisis you have to go left or right, and everyone wants to go middle. And middle is the storm…and they’re usually the worst decisions.”

Marketing is the same. You don’t get to it by consensus. You take bold positions with bold statements, and you forge your own path in the marketplace.

I hear a red flag when I ask a startup CEO about their marketing, and the answer I get is “my team will figure it out, they are working on it”, or “my team did a great job with the website”, as if they have outsourced their marketing. Well, as a CEO, if you are leaving marketing and your market perceptions to the marketing department, you are failing to rise up and be your own, authentic brand’s ambassador.

No one else but the CEO can be the standard bearer for their brand. Don’t let it be your blindspot.


34 Quotes from Jim Rohn, a Great Startup Mentor

Screen Shot 2015-02-15 at 2.10.04 PMI recently came across Jim Rohn, and quickly realized that the genius behind his work originating in the 60’s, 70’s very much applies to the world of tech startups.

Emanuel James “Jim” Rohn (September 17, 1930 – December 5, 2009) was an American entrepreneur, author and motivational speaker. Over his 40+ year career, Jim wrote 17 books. I was so eager for the quick version of his wisdom, so I found this short book of 400 of his Greatest Quotes on Kindle for 99 cents. Suffice to say, it was the best 99 cents I ever spent on anything since chewing gum. I devoured the book in a few minutes, and was puzzled to find numerous quotes that had a direct relationship to a startup’s life.

Not only that, I immediately sent the e-book as an e-gift to about ten entrepreneurs I’m currently working with, or invested in their companies, with a short note: “Everything you need to know about success is in this book.” That was the best $10 I spent. And as an experiment, I asked them if they would share with me which were the top 2 quotes that stuck with them the most, in terms of actionability.

So, I’ve chosen 34 quotes from the 400 in that book, to illustrate not only the fact that Jim Rohn was probably the original startup mentor, but to show that we don’t have to re-invent everything in the world of startup management. Starting, funding, growing, and scaling a startup requires a lot of common sense and wisdom that is already available for the picking. If you learn and believe in some basic business and life philosophies, you can use your common sense to automatically apply them, and you will often find the answers yourself.

Here are the key quotes that I liked, and a quick comment on the startup analogy.

Growth and Problem Solving

“The difficulties you meet will resolve themselves as you advance. Proceed, and light will dawn and shine with increasing clearness on your path.” – Jim Rohn If this doesn’t sound like Growth Hacking 101, I’m not sure what does. This is exactly what growth metrics and startup analytics enable you to find out. Good thing we can have that in real-time today, and in digital form. It used to all be on paper before.


“Ideas are information taking shape.” – Jim Rohn Yes, the genesis of a startup is always that magical idea. But ideas are only the beginning. You need to pad these ideas, and execute on them.

“Average people look for ways of getting away with it; successful people look for ways of getting on with it.” – Jim Rohn You can’t fool the market, just in case you were thinking about getting away with it.

“In any situation you can think of, impatience is a source of weakness and fear, while patience represents substance and strength.” – Jim Rohn It takes a while to build a viable company. Be confident, and keep strengthening your success base, one layer at a time.

“It is hard to keep that which has not been obtained through personal development.” – Jim Rohn An entrepreneur who doesn’t grow, develop and mature along their startup’s evolution eventually becomes a liability to its growth.


“Good service leads to multiple sales. If you take good care of your customers, they will open doors you could never open by yourself.” – Jim Rohn If this isn’t Customer Success 101, or Customer Advocacy basics, I’m not sure there would be a simpler way to say that satisfied customers will refer new customers back to you.

“Practice is just as valuable as a sale. The sale will make you a living; the skill will make you a fortune.” – Jim Rohn Our modern interpretation is “nail it before you scale it.”. Once you figure out that skill, you can transfer it to others and scale that way.

“To succeed in sales, simply talk to lots of people every day. And here’s what’s exciting – there are lots of people!” – Jim Rohn Another basic rule of sales is to have a large funnel.

“Even if you are new in sales, you can make up in numbers what you lack in skills.” – Jim Rohn Sales numbers speak. If you hit your numbers, nobody will say you were a bad salesperson.

Venture Capital

“Money is usually attracted, not pursued.” – Jim Rohn A similar adage is “bought, not sold”. It applies two ways: 1) Ideally, let VCs approach you, instead of you going after them, b) Strive for market pull so that customers and users come to you, and you’re not pushing yourself on them.

“Part of your heritage in this society is the opportunity to become financially independent.” – Jim Rohn Financial independence means you may not require further venture money to fund your growth.


“I remember saying to my mentor, “If I had more money, I would have a better plan.” He quickly responded, “I would suggest that if you had a better plan, you would have more money.” You see, it’s not the amount that counts; it’s the plan that counts.” – Jim Rohn You need to have a plan or strategy, and executing on that will lead you to success.

“Take advantage of every opportunity to practice your communication skills so that when important occasions arise, you will have the gift, the style, the sharpness, the clarity, and the emotions to affect other people.” – Jim Rohn If you cannot communicate with clarity, you cannot touch people or the market around you. It starts with your venture funding pitch, passes by your market and customers, and includes your employees.

“Accuracy builds credibility.” – Jim Rohn Be authentic and truthful, with your numbers and your statements.


“Their dreams were stronger than the obstacles in their way.” – Jim Rohn What a powerful statement. Just think about it during moments of difficulty.

Human Resources and People Management

“Don’t bring your need to the marketplace, bring your skill. If you don’t feel well, tell your doctor, but not the marketplace. If you need money, go to the bank, but not the marketplace.” – Jim Rohn Don’t show or acknowledge your company weaknesses in the marketplace.

“To attract attractive people, you must be attractive. To attract powerful people, you must be powerful. To attract committed people, you must be committed. Instead of going to work on them, you go to work on yourself. If you become, you can attract.” – Jim Rohn Your image as a company and as a person determine who you end-up working with, from VCs to employees to customers.

“Never attack a problem without also presenting a solution.” – Jim Rohn Beware of employees that complain without suggesting how to solve an issue.

“Good people are found, not changed. Recently, I read a headline that said, “We don’t teach our people to be nice. We simply hire nice people.” Wow! What a clever shortcut.” – Jim RohnThat’s a great human resources practice: hire people that are smart, work hard and are nice people. That’s it. The rest will take care of itself.

“He said, Mr Rohn, if you truly wish to be successful, you’ve got to associate with the right people.” – Jim Rohn It’s all about people. And that applies to your employees most importantly.

“We don’t get paid for the hour; we get paid for the value we bring to the hour.” – Jim Rohn Especially so true for remote teams. This is exactly how Matt Mullenweg, CEO of WordPress/Automattic describes his philosophy for running a decentralized organization where his employees are in several countries around the world.


“The challenge of leadership is to be strong, but not rude; be kind, but not weak; be bold, but not bully; be thoughtful, but not lazy; be humble, but not timid; be proud, but not arrogant; have humor, but without folly.” – Jim Rohn Easier said than done, but Jim Rohn has just summed-up the key management leadership qualities.

“Leadership is the challenge to be something more than average.” – Jim Rohn Read it as “market leadership” too. Unicorns, anyone? The percentage of startups that succeed, change markets and inspire others is very small. Be that one.

“The real problem is usually two or three questions deep. If you want to go after someone’s problem, be aware that most people aren’t going to reveal what the real problem is after the first question.” – Jim Rohn Jim Rohn was probably the originator of the rule of 3 Why’s? Ask Why 3 times, and you typically get to the bottom of the answer.


“Failure is not a single, cataclysmic event. You don’t fail overnight. Instead, failure is a few errors in judgement, repeated every day.” – Jim Rohn So true. Failure doesn’t happen overnight, just as success doesn’t either. Get regular check-ups with advisors and board members, so you don’t accumulate error debt.


“You cannot change your destination overnight. You can change your direction.” – Jim Rohn Immediately recognize what the data is telling you, and if you need to change direction, do it. There are many paths to reach your destination.

“You cannot make progress without making decisions.” – Jim Rohn Startups operate in dog years. It’s a fast-paced environment. The more decisions you make, the more you make great ones.

“When people asked Socrates, ‘What is wisdom?’ he always gave the same answer: ‘I don’t know’. In fact, Socrates never claimed to know much of anything except how to ask questions. And by asking questions, he would prove to other people that they didn’t know what they thought they knew.” – Jim Rohn I haven’t met a successful entrepreneur that wasn’t curious and obsessed about their curiosity.

“It is the set of the sails, not the direction of the wind that determines which way we will go.” – Jim Rohn Sailing 101. You set your sails according to the direction you want to be headed in, regardless of the wind’s direction. Interpretation: make internal adjustments to keep going forward. If the wind changes direction, just change the set of the sails.

“The enemies inside us: Indifference, Indecision, Doubt, Worry, and Over-caution.” – Jim Rohn A startup has to break new ground every day, decisively. If you prefer being cautious, get a corporate job.


“Some things you have to do every day. Eating seven apples on Saturday night instead of one a day just isn’t going to get the job done.” – Jim Rohn Ah, the old crunch time. A startup is not a university exam where you can have a sleepless night and still get an A.


“How do you deserve a fortune? Render fortunes of service.” – Jim Rohn If your startup doesn’t deliver value to the market, there is no way you will have a valuable startup.


“The philosophy of the rich versus the poor is this: The rich invest their money and spend what is left; the poor spend their money and invest what is left.” – Jim Rohn I like to see startups apply this philosophy to budget allocation after receiving funding. I like them to think that every dollar spent is an investment they are making, instead of an expense they are incurring. This applies to salary levels as well. Before paying more just because you can afford to, ask yourself whether you are always getting back more than what you are paying for.

“Earn as much money as you possibly can and as quickly as you can. The sooner you get money out of the way, the sooner you will be able to get to the rest of your problems in style.” – Jim Rohn Revenues! If you have revenues, you are less dependent on outside venture capital to survive, but you can ask for it to grow, instead.

Find Yourself

From now on, I’m going to take a more philosophical and indirect approach to coaching/mentoring startups and entrepreneurs. Truth is, as Andy Weissman pointed out, there is a Chaos Theory of Startups. In the same way that every venture capital deal is different, every startup will be different, and that chaos theory is so very true at the beginning, but as the company grows, some of that chaos turns into patterns, and it gets a little easier to manage with less ambiguity.

At the end of the day, it is the entrepreneur/startup who has to score every goal, not the coach. As an advisor/investor, all you can do is help to make them self-aware, and it will pay dividends as they’ll realize how to improve themselves and solve the challenges they will face.

Thank you, Jim Rohn.


Don’t Abolish MBOs

No More MBOs, where he puts into question the usefulness of MBO-based bonuses in startups. It’s a good read, including the discussion. I agree with Brad that linking bonuses to MBOs can be messy, so let’s abolish that. But, let’s not throw the baby with the bath water. Let’s not give away MBO all together. Let me start with a historical perspective on MBOs and its usefulness.

Startup CEO Advice: Know your Blind Spots

blind spot imageWhat can a startup CEO learn from a Fortune 500 CEO? Typically not much,- unless that Fortune company was once a startup and the CEO still thinks and operates like a startup. In a short interview with the New York Times, Francisco D’Souza (Frank), CEO of Cognizant (Fortune 2013 rank #352) shared a few lessons that will resonate with startup CEOs that are growing their companies.

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