Entrepreneur Insights

New Book from Maynard Webb – Rebooting Work

By Business Philosophy, Entrepreneur Insights, Web and Tech No Comments

Maynard Webb, former COO eBay, CEO LiveOpsMaynard Webb (one of my investors in TakeLessons and former COO of eBay) just launched his new book, Rebooting Work.

In the book, Maynard Webb identifies 4 different mindsets around work (the company man, CEO of your own destiny, disenchanted employee, and the aspiring entrepreneur). It organizes those who are self-motivated versus those who are waiting to be discovered and aims to give readers the tools to become more self-actualized, happier, and ultimately more fulfilled in their careers.

Maynard has always been the go-to guy when Silicon Valley companies have thorny problems. Whether revamping eBay’s crashing servers (transforming their technology weaknesses into a competitive strength) or investing in emerging technology start-ups, he brings strategic and operational savvy to every issue and venture.

This is his first book, and he brings this same focus to tackle outdated models of work, created a century ago, which no longer sync up with either individual or employers’ needs.

Pick up a copy. You’ll love it.


Maynard Webb book Rebooting Work

Break the Rules

By Entrepreneur Insights, Life Lessons No Comments

We were down to our last few dollars and I didn’t know how we were going to make payroll.

Our business model wasn’t working the way we planned, and we were burning cash faster than expected.

Something needed to change. Something big – and something now.

The year was 2008 and TakeLessons was working to find our place. Our best thoughts had been tested – and failed. With our backs against the wall, we did a complete 180 degree shift in our model without really knowing whether it would work. What we did know, however, is that (a) what we were doing wasn’t working and (b) there was no option to give up.

So, we broke the rules. We broke out of our current methodology and tried a radically different model.

And THAT saved our company.


Struggling on finding a breakthrough?

Ever feel trapped – confined – and can’t see a way out?

Sometimes, the right answer is forget everything you know – forget how it’s supposed to be done – and break the rules.

Break the Rules

4 Things I Learned About Business in 2012

By At Work, Business Philosophy, Entrepreneur Insights One Comment

57-504091852861cI’m a big believer in CANI – Constant and Never Ending Improvement (or Kaizen). It’s one of the core values I live by and it’s one of the joys of life.

So, in that spirit, I wanted to share with you four things I learned about start-ups, business, and life during 2012.

Lesson 1: Get the right people on the bus.

Nothing trumps getting the right team in place. And the ‘right team’ differs depending on the stage and growth of the company. Knowing when to bring in outside help is a tough skill to learn for most founders because our decisions become skewed by (a) what we don’t know – such as who else is out there that could rock the job and (b) our loyalty to the current team.

When you do hire outside, make sure you plan in advance so you have the time to thoroughly vet out the candidates.

We made a major hiring mistake at the executive level early 2012 that cost us dearly. Without going into too much detail, we got enamoured with the big company names and titles on the resume and didn’t do enough diligence checking references – both the ones that were offered, but more importantly, the ones that weren’t.

My advice for doing senior hires is to check both up and down the reporting chain. Check with their superiors (which we did) AND check with people that reported into the person (which we did not). If we would’ve looked deeper we would have found that the person we were considering was not a good match.

Brian Tracy always says to hire slow and fire fast.

Lesson 2: Put people in a position to succeed.

I’ve found that it’s not enough to get the right people on the bus. You also have to make sure they’re sitting in the right seats.

I learned this the hard way.

The company needed a Product Manager lead, so I took one of my best performing people and put them in the role. He was a quick learner and I figured he’d be able to figure out what we needed. From day one, he told me that he’d give it his best shot, but that he didn’t know what he was doing. 3 months later, the role had not advanced, the Product department was at a standstill, and one of my best guys was spending his days reading books on how to do product management.

Rather than just hire an expert in the field, I put someone in the role who didn’t understand it. Yes, he could’ve become a great Product leader, but it was going to take a year to get him there, and we didn’t have that much time.

Find people who play at things you have to work at.

If you think it's expensive to hire a professional, wait until you hire an amateur.

Lesson 3: Prepare for Rain.

One thing is for certain. It’s gonna rain. And the team that has thought through what might happen will be better prepared for the storm. In Jim Collins’ latest book, Great by Choice, he calls it Productive Paranoia. It means that those that perform the best in business assume that things will – at some point – go wrong.

The 10X winners in our research always assumed that conditions can—and often do—unexpectedly change, violently and fast. They were hypersensitive to changing conditions, continually asking, “What if?” By preparing ahead of time, building reserves, maintaining “irrationally” large margins of safety, bounding their risk, and honing their disciplines in good times and bad, they handled disruptions from a position of strength and flexibility. They understood, deeply: the only mistakes you can learn from are the ones you survive.

Collins, Jim; Hansen, Morten T. (2011-10-11). Great by Choice: Uncertainty, Chaos, and Luck–Why Some Thrive Despite Them All (p. 102). HarperBusiness. Kindle Edition.

In our company, we’re optimists. While that plays to our advantage in most cases, we’ve learned that it can be a detriment if we fail to protect the downside.

In 2013, we’ve decided to do things a bit differently.

We still believe we can conquer the world (of course we can!), but we are putting in place definitive finance contingency plans just in case we’ve overestimated our ability to perform. This gives us a fallback plan that allows us to react quickly to several market scenarios and bounds our downside risk.

This does not mean we are risk averse or shying away from big plan. Oh no. Just the opposite actually. We have bigger plans this year than we’ve ever had. However, in addition to the optimistic plan, we have a strategy to protect us in case those plans go awry. We know where we need to be

Lesson 4: Life is an Ebb and Flow

I live in San Diego and regularly get the pleasure of watching waves come crashing into the sand. Then, just as easy as they roll onto the beach, they subside back into the ocean.

Business is a lot like that. It’s filled with highs and lows – ebbs and flows.

What I learned was to not let the highs get me too high, or the lows get me too low. Just as everything seems to be going our way, there’s always a next unexpected slap to the face. And, when I have my “oh shit” moments, I can rest easy knowing that ‘this, too shall pass’.

This helps me have the resolve to fight on in the darkest of hours, and it keeps me from believing my own bullshit in the good times.

Question for you…

What business or life lesson did you learn in 2012?


The Importance of Mentors and Your Chance of Business Success

By Business Philosophy, Entrepreneur Insights, Leadership No Comments - Successful People Seek Mentors

I’d love to say that my best ideas were formed inside of my head, but truthfully, the biggest breakthrough’s I’ve had are because I was able to take the raw thought material in my head and receive insights from other smart people.

If you’re smart, that’s a good start. But someone not as bright can play at a much higher level by getting the help of others.

For me personally, mentors have played a critical role in my business. Each time I’m faced with a seemingly overwhelming set of circumstances, I lean heavy on the men and women in my life who have been there and done that. Why would I want to try to figure it out myself? No way! I’d rather learn from the experiences of others and not have to go throug the pain.

Mentors play another key role. Many times, they don’t tell you the answers to your problems. Instead, they help you ask the right questions. I’ve been so deep in a situation that I can’t see alternatives other than what I’ve been thinking about. Smart mentors help you take a step back and look at the problem form another viewpoint. And sometimes, that’s all you need for a major breakthrough.

Who are your mentors? It’s good to have them in business as well as your personal life. Mentors are people who add value to you by providing you with another way to view the world.

A great mentor never gives you the answer. They only help you ask the right questions.



The Life of a Startup

By Business Philosophy, Entrepreneur Insights, Start-Ups, Uncategorized No Comments

Here is an email I sent this morning to my team. First, I wanted to have them see that most startups go through the same struggles that we go through. Second, I wanted them to know that I have full confidence, faith, and trust in their abilities and that I see them as leaders within our company.

The email features a blog post by Mark Suster of GRP Partners called Entrepreneurshit.



I hope the week is going well.

I’m outside on a patio in Kauai doing a little reading and contemplating.

I’ll be doing that a lot this week, so you may get more emails. 🙂

Below is a link for an an article I just finished from Mark Suster on the real life of a startup. I met with Mark during our last round. Good dude.


The takeaways:

Sometimes I get frustrated and I wonder if we’re the only company struggling to find market fit. Are we the only ones that got off track? Does anyone else have issues with hitting metrics? Why in Gods name can’t we get a teacher application that works better? How do I get the entire company to move faster?

The truth of the matter is that these things are fixable and will pass. Doing a startup is not glamorous – full of highs and lows, almost-wins, and busted quarterly plans.

However, what will see us through is that we, as a team, (a) never doubt our outcome (b) challenge each other to get better, (c) learn quickly and apply those learnings throughout the company, (d) have each other’s back (e) work towards truly creating value for the people we serve.

As you start prepping for next year, I want you to raise the bar – for yourself, your team, and each other.

Start thinking about what you want to get done next year. Design your life. Require more of yourself, and judge your own success based on how well you are helping your team succeed.

YOU are the leaders of this company; I want you to digest that – own it – let it settle in. When this company makes it, you will be the reason.

Today, ask yourself, “How do I raise my game next year?”, then take action to do it.


Things I Learned at the Crosslink Startup Investor Meeting

By Entrepreneur Insights, Start-Ups, Venture Capital 2 Comments

Crosslink Capital

Recently, I got to attend the Crosslink Investor Meeting where partners of the firm spoke on what their seeing in the marketplace.

A couple key takeaways for me was that technology and the internet is still very early. Lots of room for growth and expansion as software eats the world. Second, some of the largest inflection points in a business are made when you get the right team. Never underestimate the power of the team.

Here are my notes.

Takeaways from The Crosslink Conference

Why We are Growth Equity focused

  • Different investing and operational skill set than steady-state or slower-growth
  • Moore’s law is open to everyone.
  • In 14 years, Google has surpassed MSFT in market cap. Go where the growth is.
  • The internet will expand to most all service businesses.

Characteristics of winning start-ups

  • Market dynamics matter. Industries and macro trends are important.
  • Winners make most of the profit. Be early. Be flexible.
  • Many inflection points with winners. Again, be flexible.
  • You must understand the value proposition.
  • Many losers.
  • Hard to value.
  • The rate of change is changing faster and faster. Thus, the only ones who can keep up are those who are growing.

Building a company boils down to these four things:

  • People
  • Products
  • Strategy
  • Execution

View of the Market

  • We expect a long road ahead
  • Deleveraging underway – especially in financial and consumer
  • We see stocks still inexpensive relative to bond yields since 2008
  • Cyclical growth recovery is over. Thus, we have to be in growth companies.
  • 10% a year for the next 3 years feels about right for the S&P

Eric Chin – Partner (and TakeLessons Board Member)

The questions we ask when investing:

  • “What is your key differentiator? Your secret sauce?”
  • “How defensible is the secret sauce?”
  • Does it fit in our themes?


  • Still very early. Less than 20% penetration.
  • Supply chain, business intelligence, enterprise is a big area.
  • Multiples are correlated with growth rates
  • 30% growth = 6x revenues multiple
  • Start with the end user in mind. Build software for the person who uses it the most. Usability is absolutely a must. If not, there’s no adoption.
  • Celebrate simplicity of use.

Advertising Technologies

  • Total advertising $175B market and growing. Online is now $40B.
  • Brand Spend, Video, mobile emergence, and real-time bidding.
  • MARIN Software had a great video that explains what they do. – Chris Lien, CEO. Good dude. Very smart.

Brian Grey – Bleacher Report

  • Focus on building a brand
  • Four D’s of fundraising: Discussion, Diligence, the Dance, the Drama – prepare for all four because they will happen – especially the drama.
  • Choose investors carefully and wisely. Not all are on the same level.


Goals: Winning at the Little Things

By Entrepreneur Insights, Goals, Life Lessons One Comment

At the end of each quarter, I take a detailed look at my yearly goals to see how I’m progressing against them. Sometimes I’m ahead – sometimes behind. And what I’ve begun to notice is that I’m ahead on the items where I accomplish smaller tasks more frequently.

There’s a concept in goal setting called “chunking”, which means taking a large daunting task and breaking it down into bite-sized ‘chunks’.

For instance, I want to become a better public speaker, so I made a commitment to speak 12 times this year. (I surpassed my goal already). The way I broke this down was, in January, to list the topics that I felt like I could add value to a conversation. From there, I started talking to friends and contacts in the industry and offering to speak at their events and seminars.

My goal – chunked down – was to (a) understand what I’m good at, (b) prepare a presentation, (c) make contacts, and (d) go speak.

12 speaking events for the year is one per month. So instead of asking myself how I could do 12 in a year, I asked myself what I needed to do THIS MONTH to speak once. This made the larger task more plausible.

Susan Butcher is an American dog musher, noteworthy as the second woman to win the Iditarod Trail Sled Dog Race in 1986, the second four-time winner in 1990, and the first to win four out of five sequential years.

I was in the bathroom at a restaurant the other day and read a quote from Susan. I liked it so much that I took a picture of it. (By the way, it’s cool that a restaurant had this wallpaper in the BATHROOM!)

…You don’t win because you do one thing or two things right. You win because you do one thousand little things right throughout the year.


Quote by Susan Butcher

The Goals Takeaway

I believe we have a tendency to suppress our wants and goals because we can’t see how we can get there. But the truth is, you don’t need to. Not all the way at least.

All you need to be able to see is the very next step.

Let’s say you get in your car from Detroit with a plan to visit the Pacific Ocean. All you need to do is see the road in front of you, have a good GPS, stop and refuel, and keep driving. Even though you won’t see the ocean for 95% of the trip, you’ll get where you need to go.

Just take the very next step in front of you.