Rediscovering Ourselves: Navigating Identity in Life Transitions

person with body painting

Letting Go of Identity. Such a tricky and painful process during change. We hold onto the past, onto our old identity & reality and it drags us under the water like holding onto a log floating down the stream. The log has passed and no amount of clinging or wishing will change the reality of […]

Managing Life’s 8-10 Year Cycle (part 2)

TLDR: “Roughly, every eight to ten years, life seems to cycle through like a brush fire to clean up the excesses of the past decade.” The current cycle never ended as planned. As the cycle moves to the next cycle, people feel ungrounded and seek even deeper for purpose and meaning. There are proven tools to navigate […]

The Importance of Getting Small

I was asked to write a guest piece for Spark this week and reposted here. As we all work to manage through the changing cycle, I keep hearing from friends, entrepreneurs, and clients that they are struggling with their identities, their purpose/focus, and feeling like they are enough and doing enough. The answer is learning […]

Remembering When Elon Almost Went Under

To all the aspiring entrepreneurs battling through COVID: With the hopeful Crew Dragon launch on Saturday, Elon will show us yet again what the human spirit is capable of and usher in manned space flight’s next chapter. However, I remember & experienced when not one but all three of his companies were on the brink […]

The Two Arrows: Productive Pain vs Unnecessary Suffering

A lot of things seem upside down in the world right now. Many plans or dreams are deferred, if not upended and we feel anxiety in the face of uncertainty. However, this is a core part of flourishing. In entrepreneurship and in life, disappointment (AKA pain) is inevitable. However, suffering, which drives most of our […]

Embracing Life’s 8-10 Year Cycle

Roughly, every eight to ten years, life seems to cycle through like a brush fire to clean up the excesses of the past decade. I’ve experienced this both on a personal and business level four times now (in addition to the 1987 one day 23% market drop).  The Great Financial Crisis cycle has abruptly ended […]

If I Lose My Fear, Do I Lose My Drive?

I hear this a lot from entrepreneurs and students. “If I lose my fear, do I lose my drive?”.  Two things are implicit in this question…1) fear/anxiety is an essential motivator for success and 2) being driven by anxiety & fear (often a default) has an unsustainable & unacceptable cost. This is a false trade-off…success […]

Hypothesis: Do You Know the Bet You’re Making?

Since the future is unknowable, by definition, we are all making bets in our life, testing hypotheses and probabilities. However, often, we aren’t aware we are making a bet or what that bet is. As a result, we don’t prioritize nor focus on the key things. This applies to careers, relationships, schools or starting companies […]

Enough: Your Savior or Your Demon

My partner, Carter, has hypothesized “…that behind every driven CEO is a 6 year old child seeking its parents’ approval”. In these formative years, we start the dance with being enough (and feeling we aren’t enough). We create coping mechanism to deal with this discomfort whether it be over-achieving, addictions, Instagram posts, compulsive behavior, etc. […]

The Dawn of a New Era in VC & Tech

Tech and VC are entering the Dawn of a New Era. Our industry goes through thematic cycles roughly every 10 years (in addition to the “15 year tech” cycle).  The 2020’s will be known for the rise of Stakeholder Capitalism. We will significantly change how we build companies and what their greater roles are. There […]

The Three Drivers of Contentment & Motivation at Work

What motivates us to perform and drives contentment at work? Most entrepreneurs struggle with this question. You want success, want to have drive and yet rely too heavily on fear-based or external motivators which often leave a negative residue. The research shows that the most effective motivators are intrinsic and positive. A champion needs a motivation […]

Which Wolf Do You Feed?

Question: If you lose your fear, do you lose your drive?  It’s a question many entrepreneurs ask themselves.  They seem to have bought into the idea that you can either be content or you can be driven, but those two states cannot coexist. But that idea is flawed. In reality, we are the stories we tell […]

VC Confidential Is Now Something Ventured

Something Ventured is pretty fully operational! Back in 2005 when I was on the FeedBurner board (Twitter 1.0), I started VC Confidential with two goals: 1) to help entrepreneurs see behind the VC curtain on how we thought/made decisions and 2) to see how the FeedBurner RSS service worked in practice. Dick Costolo (CEO), Brad […]

My Venture Covenant With Entrepreneurs

There is a false dogma around the VC/Entrepreneurship relationship…supported by bad behaviors on both sides. You feel a need to manage your investors & board, to not show weakness and present to us. We fail to fully listen, dictate desires or fears and financially optimize our investments. Trust and open communication are our most precious […]

Multiples vs IRR

One of my most popular posts from VC Confidential… “You Can’t Eat IRR.” — anonymous I was at a business school today helping judge several business plans. As group after group presented, I saw each make the same mistake as the previous. When they tried to justify the investment from the perspective of the VC, […]

Real Is Mandatory

Real Is Mandatory “Then you better start swimmin’ or you’ll sink like a stone For the times they are a-changin’.”  — Bob Dylan The venture markets are a-changin’ with investors and public markets demanding rational business models, visibility to profitable growth and inherently sound economics. Companies like Homejoy and Sidecar have gone under while stars like […]

The Key Israeli Story: StartUp Nation

Larger Post coming…without appreciating the context (yesterday’s post), it is hard to fully grasp the origin nor significance of the tech renaissance that is taking place in Israel.  One has to see it to fully appreciate it. Much like Boston and Silicon Valley had its origins in military R&D and culture, Israel’s tech ecosystem also […]

Stunning Day in Jerusalem…Day 1

Quite the first day…cultural day in Jerusalem (minus our guide saying “all schools have cancelled trips to Jerusalem given events this week…”).   Landed at 8:30am and off to the races. We visited the Old City where we walked through the four quarters, touched the marble Jesus was supposedly laid on (post Cross) and the […]

To Change the World, Start by Making Your Bed

As many of you may know, I am a commencement speach junkie. One of the stars of this year’s batch is Admiral McRaven’s talk at UoT. He is a navy seal, Commander of the United States Special Operations Command & oversaw the final raid on Osama bin Laden. This has been going viral (approaching 2M views in 1 […]

Millennials: Rightly Up-ending the Apple Cart

“When you come out of the storm, you won’t be the same person who walked in. That’s what this storm’s all about.” ― Haruki Murakami, Kafka on the Shore While the Boomer's bemoan (wrongly) Millennial's lack of work ethic, narcissism and lack of respect for seniority, there is a sea of change coming that corporations and start-ups alike […]

17 Fundraising Ideas

Our portfolio company, GiveForward, is one of the standout "double bottom line" companies around. They help people with medical needs (and other) raise money to pay the bills. To date, they have raised $62 million for people. Given that 60% of personal bankruptcies are driven by mounting medical expenses, they have helped a large number […]

The Quest to Get Better

My friend, Brian Johnson, just posted on an awesome topic…Getting Better vs Being Good. Entrepreneurship is not only tough — it is non-linear and success often opaque. Also, short video link below of Carol Dweck's Mindset work…definitely worth everyone learning more about this. The key to managing this reality is: 1) to know your Northern […]

Success on Your Terms

I increasingly have conversations with both rising and established entrepreneurs around “what is success and why does it not feel fulfilling?” Peter Drucker, the uber-management sage, said that as more people acquired wealth, they would shift to focusing more intently on making a purposeful impact on the world. The Millennials are focused on parallel tracking […]

Curiosity, Obsession & Dogged Endurance

“I know quite certainly that I myself have no special talent. Curiosity, obsession and dogged endurance, combined with self-criticism, have brought me to my ideas” — Albert Einstein As I look back over my life, the most successful or content people I know were not the most brilliant but the most determined and disciplined. Excellence […]

Success vs Struggle: The Art of Compartmentalizing

Ryan Blair posted an interesting piece The Five Steps of Compartimentalization in Forbes last year.  I did an exercise I try every couple of weeks where I lay out all of the commitments I had made ranging from board meeting follow-ups (intros, offsites, etc) to family matters (coaching, attending, traveling) to new deals (diligence, meetings, […]

What Entrepreneurs Don’t Tell You about the Fight

A little perspective from up North. Our Canadian portfolio CEO, Guy Gal, forwarded over a great piece from StartupNorth titled The Things an Entrepreneur Will Never Tell You. It is definitely worth a quick read as entrepreneurs often feel they are unique in what they are going through in terms of high's & lows, feeling […]

Some MoreTeddy for the Weekend

A little something for you all laboring to improve the world through your entrepreneurial efforts (from my friend, Brian Johnson at Entheos.com). Have a great weekend:) “Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much […]

Inverse Paranoia

Love this concept which my friend, Brian Johnson, posted recently.  Great entrepreneurs have a sense of "inevitability" in the belief in their idea and mission. Jim Clark refers to it as "willing a company into existence".  “My earliest mentor, W. Clement Stone, was once described as an inverse paranoid. Instead of believing the world was […]

Entrepreneurs’ Manifesto: Shame In the Arena

Great TED talk by Brene Brown on Shame and its role in innovation and society. YouTube Link to Brown Shame Talk: http://www.youtube.com/watch?v=psN1DORYYV0 Terrific Roosevelt quote from it for all you entrepreneurs in the arena…I'll call it the Entrepreneur's Manifesto: "It is not the critic who counts; not the man who points out how the strong […]

A Proud Father

Every once in a while, as a father, your children do something that amazes you and makes you incredibly proud to be a parent. My daughter was selected as one of fourteen United Nations GirlUp Ambassadors from over 400 applicants. She had been inspired, after reading Half the Sky, to travel around the US, raising […]

Pura Vida — Life and Entrepreneurship

"[Pura Vida] embodies a philosophy in which communal ties are strong and close; difficulties are overcome with a resilient and happy spirit, where life is enjoyed leisurely and to the full, and where fortune of whatever size is heartily celebrated."  – Tony Cousins I have spent the past week in Costa Rica surfing, doing yoga, eating, […]

Ask the VC

Erik Severinghaus sent over this hilarious xtra normal video on Stupid Questions VC’s Ask that has been floating around the internet. Erik is an awesome, serial entrepreneur and I’m certain has had more than his share of these fine interogations. Since I focus on showing entrepreneurs behind the VC curtain, here you go:   Stupid Questions […]

Karma Kitchen: Most Intriguing Restaurant

Rishi Roongta works with me at New World and is omnipresent. He is curious and tests just about everything under the sun. He came across a new restaurant that redefines both Paying Forward and restaurants in general. As he writes: “Karma Kitchen was pretty awesome. I was a “waiter” and served tables for 4 hours.. […]

Follow Your Bliss — Finding Joe

Joseph Campbell is the most influential person to have impacted my life. He was the world's leading mythologist and had an amazing capacity to show the common threads that cut across all religions, movies, books and stories. An awesome movie just came out about him and The Heroe's Journey that I have mentioned to everyone […]

Enough With the Gloom & Doom on Groupon

In 2000-2001, I remember reading negative article after negative article on Amazon. It was burning money quickly, e-tailers were going under left and right and brick & mortar stores were re-asserting themselves. People kept a diligent death watch for it after the demise of Webvans ($1b) and others. In reality, what was going on was […]

Seek First to Understand then to be Understood

When you've been in the venture business as long as I have, you have seen your share of dysfunctional, poisonious board/management situations. None of these needed to occur. They all fall into the "life's too short" category. Understanding, alignment and unification (leave your ego at the door) are the key elements of avoiding this.  For […]

Carter Cast on the “Drama of Comparative Living”

My friend, Carter Cast, gave a wonderful talk to a large group of Fortune 500 executives and non-profit leaders. I highly recommend everyone reading this to take this to heart given where Carter comes from. Carter has had a career unmatched by most I know. Starting as one of the star swimmers on Stanford's national […]

Synchronicity in Everyday Life

"A connecting principleLinked to the invisibleAlmost imperceptibleSomething inexpressibleScience insusceptibleLogic so inflexibleCausally connectableYet nothing is invincible" — the Police, Synchronicity   People, places and events come into our lives for a reason. We rarely fully appreciate or even notice them. Often we'll observe a confluence of them and comment on what a "coincidence" we've experienced. Well, after […]

Need Help Finding Mobile/iPhone Apps?

My long-time Kellogg/BCG friend, Al Warms, has gone public with his latest effort, Appolicious.  Al sold his previous company, Buzztracker, to Yahoo and went on to successfully run & grow Yahoo News. Appolicious is a community for application discovery. You can upload your current applications (names only) and the site will begin to profile your interests […]

Strategic Protectors

In difficult times, strategic partners can be essential to survival. As companies fight for air in these cash strapped times, larger corporations have valuable resources. Our portfolio companies have leveraged partners in several ways. 1) Pre-paying revenue. Some customers will pay in advance of delivered goods. Future takedowns are applied against this. 2) Venture leasing: […]

The Art of Selling Your Firm

Despite the markets’ gyrations, 2008 was the best year for liquidity in our firm’s history. In fact, our largest exit (Lefthand Networks) closed in November in the heart of the downdraft. In looking across these exits, the strong exits all had several common elements: 1) Self-sufficiency: the old saying in venture is that companies are […]

Term Sheet Tool

The gang at Wilson Sonsini have created a very interesting term sheet generator. In addition to its practical value, it is also an interesting educational tool. If you are an entrepreneur or a new VC, it goes through all of the key term sheet elements in very specific details with the most common option highlighted […]

Why Great Companies Get Started in the Downturns

I have always been amazed by how many of our success tech stories, as well as Fortune 500 companies, started during drastic down turns. Innovation does not take a holiday, and in fact, thrives during difficult times when pain & need are greatest. While the current downturn is historic, it pails in comparison to the […]

Why VC Returns Languish

So you see a pattern here? Number of VC-backed IPO's:1995    2051996    2721997    1381998      681999    2502000    2022001      222002      202003      232004      672005      432006      562007      762008        7 (none in Q2 or Q4!) Average Time to IPO1998    3 years2008    9 years Number of Companies Funded:1998    1,896 ($14.0B invested)2008    1,930 ($14.1B invested) When you cut through all of this data, […]

Josh Lerner on Serial Entrepreneurs

"A good hockey player plays where the puck is. A great hockey player plays where the puck is going to be."        — Wayne Gretzky peHUB had a recent post by Connie Lolzos on Josh Lerner's recent research about serial entrepreneurs. There are two general camps. One states that success begets success and serial entrepreneurs […]

Apple Slices

I came across an article from last year from Fortune, Steve Jobs Speaks Out, in which Steve discusses Apple's approach to business and innovation as well as its culture. Entrepreneurship is part passion & execution and part mentoring. The best entrepreneurs continually learn from the examples of those around them. They are curious about what […]

…Or Assuredly We Shall All Hang Separately

"We must all hang together, or assuredly we shall all hang separately." — Benjamin Franklin at the signing of the Declaration of Independence Dan Primack set off an interesting dialog around his article Radically Reinventing Venture Capital. There is a growing wave of articles about new or revised models and debate around what went wrong.  […]

The Riskmaster

Tim Draper has recently launched his blog, titled "The Riskmaster" (http://theriskmaster.blogspot.com/).  He will post on the venture capital business, spreading entrepreneurship, interesting videos and inspirations on the economy.  This blog is guaranteed to be entertaining, informative and challenging. For those of you not familiar with him, Tim is the founder of Draper Fisher Jurvetson and […]

If Larry and Sergey Asked for a Loan …

"Be fearful when others are greedy, and be greedy when others are fearful."            — Warren Buffett Well, there is no doubt that fear is running rampant through the streets. This will provide a great opportunity for entrepreneurs to take advantage of market inefficiencies not seen for decades. Those that intelligently manage the downside, will be […]

Be Careful Who You Deal With

As these markets continue their chaotic path downward, people's true colors come out. Some people show increasing amounts of fairness and consideration. Others will self-optimize and use every bit of leverage that they can get their hands on. Two entrepreneur friends of mine recently had a very negative experience with an investor who has a […]

What Compensation Should You Give Your Team?

One of the most popular search topics on my blog has always been compensation. I thought I would lay out historically the average benchmarks with some caveats. The first caveat is that these numbers will be skewed more towards an early/expansion stage company versus a start-up or late stage companies. The second is that with […]

What Are Some of the Hedge Guys Doing Now?

After the downdrafts, you would assume that people would be jumping into market to bottom feed. However, a number of the smartest guys have massive cash positions. Clearly, they are waiting for the other shoe to drop. From a recent Whitney Tilson piece:"These are smart guys, but I think they're wrong here — and think […]

How Long Will This Downdraft Last?

"Nobody told me there'd be days like theseStrange days indeed, strange days indeed"                    — John Lennon I have written on several occasions about the likelihood of a correction and pull back in the venture market. I've also said that it will be triggered by a correction in the stock market which […]

If You Are A Woman, Head to the Midwest

In reading through the recent Fortune article, The 50 Most Powerful Women, I noticed that half of them were in the Midwest. This included: #2 Irene Rosenfield    CEO, Kraft#3 Pat Woertz            CEO, Archer Daniels Midland#7 Susan Arnold        President, Proctor & Gamble#8 Oprah Winfrey      Chairman, Harpo#9 Brenda Barnes     CEO, Sara Lee This […]

The Pixar Magic

I love stories about entrepreneurs and inventors who overcome adversity, flirt with disaster & bankruptcy, only to end up hitting the long ball.  The Economist published a great article in May describing the Pixar story.  As usual, things did not start off in a very promising manner. "Ed Catmull's ambition at school had been to […]

“Why aren’t VCs freaking out as Wall Street burns?”

Interesting Piece from PEWeek: "Why aren't VCs freaking out as Wall Street burns? It's a question that I've been asking for more than a week now. There is, of course, the usual litany of responses: we're long term investors, we invest in fundamentals, our LPs are going to be good for their commitments because they're […]

Rough Ride Ahead: Buckle Up & Get Your Money Now (if you can)

"Thus far in the second quarter of this year, there have been NO venture-backed IPOs.  There has never been a quarter where this situation has occurred (since NVCA has been tracking such data). "  — NVCA Mailing I am pronouncing this cycle official dead at Q2, 2008. We have a general VC cycle that lasts […]

TechCocktail Conference Chicago

Eric Olson and Frank Gruber are launching their first TechCocktail conference in Chicago this week on Thur, May 29th at Loyola University. You can register by clicking here. They have pulled together a great set of panelist including Dick Costolo from FeedBurner/Google, Jason Fried from 37Signal and a host of other luminaries. They have also […]

The VC World Inflates as Well

Following up on my post on the buyout world, the VC world has also experienced valuation inflation over the past year. As more and more liquidity comes into the sector (mostly acquisitions), VC’s are beginning to feel bullet proof again. We are starting to see VC’s promising entrepreneurs $80m and $90m pre-$ valuations if they […]

Blodgett Helps Explain the SubPrime Isse…

And we wonder why Buffett says that the credit markets are redefining the term "junk" debt… How Citi, HSBC, Morgan, Et Al Vaporized Billions Henry Blodget | November 28, 2007 9:07 AM Mystified about how Wall Street’s best and brightest could suddenly up and lose tens of billions of dollars on insanely risky mortgage bets? […]

The Art of the Start

Ironically, I drafted the following post at the same time my friend, Jim Stamos, sent me Marc Andreessen’s recent post about the current writer’s strike in Hollywood Rebuilding Hollywood in Silicon Valley’s Image. "Last week I posted a rather pointed polemic titled "Suicide by strike" in which I argued that the big entertainment companies were […]

Other People’s Money

"There’s only one thing I love more than money. You know what that is? OTHER PEOPLE’S MONEY. " — Danny Devito in Other People’s Money I haven’t posted in a while as work has been absolutely chaotic as the pre-Thanksgiving rush has begun. Start-ups, acquirers, partners are all pushing to close transactions before our business […]

Out of Sight, Till Now, and Giving Away Billions

In yet another example of the new wave & breed of philanthropists, Feeney made his fortune in duty-free shops. In Out of Sight, Till Now, and Giving Away Billions, O’Cleary gives a taste of what is in Feeney’s upcoming biography The Billionaire Who Wasnt: How Chuck Feeney Made and Gave Away a Fortune Without Anyone Knowing […]

Corporate VC’s Up Their Activity

Vineeth forwarded this article onto me: Google’s new role: Venture Capitalist. In yet another sign of where we are in the cycle, strategic VC’s are accelerating their activity. Strategic activity tends to peak (along with angels’) right before a market pull back. Google may be a different animal, but many of the strategics are diving […]

TiECON 2007

TiE Midwest is holding its annual conference on October 5th from noon to 6 at the Hyatt Regency in Chicago. This is a great event and this year, they have the dynamic and always interesting brothers, Glen (CEO of Allscripts) and Howard (founder CCC & CEO of Flashpoint) Tullman keynoting. Definitely worth the time if […]

Keeping Perspective

My wife sent me this article. She is on the Women’s Board over at Children’s Memorial and comes across  these stories often. Talk about keeping things in perspective. No matter how hard my working world becomes, it is nothing compared to this one… The Night RoundsThere’s no darker place than a children’s hospital at night. […]

Business Musings From Carter Cast

I was having breakfast the other day with a friend of mine, Carter Cast, and we were discussing the dynamics and effort necessary to successful build an entrepreneurial company into a larger organization. Carter is a great guy and well known for his balanced approach to management and the effort he spends on building effective […]

Too Much Information

I am increasingly coming to the conclusion that it is temperament & emotional behavior and not intelligence/insight that drives the majority of successful investing.  Knowing common behavioral traps and being aware of your own behavior is key to becoming a truly successful investor. Excessively relying on information is one of the behavioral traps that researchers […]

Term Sheet 101: Preference

Nearly all VC’s use convertible preferred stock as their vehicle of choice. Most entrepreneurs know this but many don’t fully understand the different flavors and elements of it. Preference refers generally to the seniority of a given class of stock versus others. Preferred A stock usually gets paid back before common and follow-on Preferred issuances […]

Term Sheet 101: Preference

Nearly all VC’s use convertible preferred stock as their vehicle of choice. Most entrepreneurs know this but many don’t fully understand the different flavors and elements of it. Preference refers generally to the seniority of a given class of stock versus others. Preferred A stock usually gets paid back before common and follow-on Preferred issuances […]

Sea of Change

One of benefits of being in venture capital is that you can see activity and trends across a broad array of industries. Additionally, you spend a considerable amount of time talking to people about deals, career changes, financings or general assistance. You can also get a sense of how certain companies are doing based upon […]

FeedBurner Pro Stats for Free Now

I have been using the FeedBurner stats PRO and MyBrand services since day one and paid the monthly fee. FeedBurner recently announced, in Google customary fashion, that these both will now be available for free to all users. Definitely worth checking out if you are using or have considered using FeedBurner’s core service to manage […]

FeedBurner Pro Stats for Free Now

I have been using the FeedBurner stats PRO and MyBrand services since day one and paid the monthly fee. FeedBurner recently announced, in Google customary fashion, that these both will now be available for free to all users. Definitely worth checking out if you are using or have considered using FeedBurner’s core service to manage […]

The Power of Technology & the Knowledge Economy

The most recent issue of Institutional Investor (its "40th Anniversary Issue") has a series of interesting perspectives from the pioneers and leaders of the financial world ranging from John Bogle & Warren Buffett to Arthur Rock & Henry Kravis. If you can chase it down, it is quite the interesting read. One of the pieces […]

Teach A Man to Make Cell Calls…

"Teach a man to make cell calls, and he eats for a lifetime…"  — Matt McCall Home run blockbuster companies have historically driven both the venture and entrepreneurial worlds. Large infrastructure plays (like Cisco) and service plays (like Amazon or eBay) have defined this landscape. However, with the tepid IPO market impairing exits for the […]

AsktheVC: How Do You Calculate Operating Cash Flow

Yesterday I posted the following as a guest blogger to Brad Feld’s and Jason Mendelson’s popular blog, AsktheVC. Matt takes on the following question: What are some of the best ways you’ve seen to sensibly estimate and/or calculate capital and/or operating cash flow, and how do you like to see this presented to an investor? […]

GP Consolidation Part Two

I posted last week about the consolidation of the venture capital industry. Whitney Tilson recently pointed out that this is also happening in the hedge fund world. LP’s will increasingly gravitate towards brand where they also have the added benefit of being able to deploy larger sums into larger funds  (versus a lot of smaller […]

Fidelity Comes to VC

The shakeout and consolidation in the venture business continues forward at a strong pace. Brand and scale are increasingly driving success. The larger the venture firm, the greater the in-house domain expertise and the wider the breadth of deals in each vertical. In an effort to simplify the guessing involved with picking funds, institutional LP’s […]

Using Scorecards With Your Board

KPI (key performance indicators) scorecards are essential in managing a company and communication with a board. KPI’s are the key metrics that capture the specific performance of each key area of the company. These vary both by industry and by company within each industry. Most companies seem to by-pass Scorecards.  In selecting KPI’s, they should […]

How to Divide the Pie

Sam Martin sent in an email asking about determining founder equity. "What amount/percentage of equity is usually reserved for the founder, CEO, and management team.  Is there a rule of thumb for how you determine who should receive equity and who shouldn’t?  What is a common vesting schedule–if there is such a thing?" Great questions […]

Real Estate Is Toxic

When venture capital and real estate mix, something has gone terribly askew. I am not talking about innovative companies like Zillow or Realtor.com but rather old fashion real estate ownership. One of the least understood liabilities for entrepreneurs is their long term lease. Some firms go as far as to sink significant sums into buildouts […]

The Big Meltdown

This Krugman piece, The Big Meltdown, appeared recently in the NY Times. As I have said before, there is a lot of irrational behavior going on in both the public and private markets. Debt remains high, all asset classes have seen big rises and investors, hungry for the rush of another "hit", stretch further and […]

Bataan Death March

The venture business runs between the goalposts of greed and fear. This is no more apparent than during a funding event. Entrepreneurs are often puzzled by why another company’s funding erupts into a feeding frenzy, while their fundraising drags on like "the Bataan Death March." While no one can ever capture all of the intangibles, […]

How Did the Superbowl Ads Fare?

Comscore recently released the results of their consumer survey that quantified "Americans’ attitudes and opinions related to Super Bowl XLI." In my Doritos post this week, I mentioned the various benefits that Frito-Lay gained from their user generated ad strategy. Not only did they get significant buzz/free publicity and lower production cost on the ad, […]

Venture Philanthropy Podcast

As you all may know, I continue to get more involved withe world of venture philanthropy. Much like venture capital, if done well, drives innovation and change into the corporate world, I believe that venture philanthropy can also positively impact traditional philanthropy. I’ll define what I view as key principles to venture philanthropy in a […]

VC Board Best Practices

How ironic…I did a post yesterday about how disfunctional venture backed boards can get and behold, a new white paper "The Basic Responsibilities of VC-Backed Company Directors" from a consortium of venture groups comes out on best practices regarding boards. "The paper’s basic premise is that VC-backed boards are particularly prone todysfunction, due to: (1) […]

The Myth of 51%

One of the greatest misperceptions in the early stage entrepreneurial world is that control revolves around maintaining greater than 51% ownership in a firm. In many term sheet negotiations, I have seen entrepreneur after entrepreneur focus intently on maintaining majority ownership. While this is key for buyouts when the company is cash flow positive, it […]

Queen Elizabeth Struck By Novo

My friend, Jim Kalishman, sent me the following link (Flu Outbreak Sickens Hundreds) about a recent outbreak of the Novovirus on the Queen Elizabeth 2 that took down 17% of the passengers. They mentioned that sanitizing poker chips and not allowing self serve at buffett limited the spread. Makes you think twice about grabbing that […]

The Power of Dry Powder

One of the hardest things to manage in early stage venture capital is asset allocation to specific investments across the portfolio. You strive to maintain diversification by investing across 20+ investments and hope that you maintain adequate reserves to support your companies, can get enough capital into your winners and avoid plowing prodigious amounts into […]

Gates: The Way We Give

You are increasingly going to hear me write about Venture Philanthropy and Social Entrepreneurship. I see a blending or cross over starting to occur between the venture/entrepreneurial world and the philanthropic one. Both sides can benefit from approaches and axioms of the other. Just as in our economy, you need to continually innovate and find […]

Dancing with the Novovirus

A pessimist sees the difficulty in every opportunity;an optimist sees the opportunity in every difficulty. ~Winston Churchill Historically, yearend has been a slow time in the venture world. From Thanksgiving through New Year, firms focused mostly on wrapping up loose ends in their portfolios. Last year, as echoed in the public markets, ended with a […]

Geras on Integrity

Bob Geras, perhaps Chicago’s most prolific angel investor, sent me an email with the following quote from his dad. I liked it and thought I’d pass it along: "Money and success come and go. What’s really important and lasting is your integrity, reputation and self respect. It’s really very simple. Treat others the way you […]

Pursuit of Happyness

" We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness."— Declaration of Independence I saw a very intense movie with my wife and another couple just before vacation called […]

Fifth Financial Center/Women Pirates

The surprising answer is that the Cayman Islands is the Fifth Largest financial center in the world. This tiny island, because of favorable tax treatment and a host of other things, has become home to many off-shore vehicles, especially hedge funds, private equity funds and such. Amazing… For those interested more in the stories of […]

Wall of Worry

"The temptation to quit will be greatest just before you are about to succeed."— Bob Parsons, founder of GoDaddy (supposedly from a Chinese proverb) It occurs so frequently that it has become a cliche. The entrepreneur who is on the verge of dismal failure, grinds it out and builds a successful business. In many ways, […]

A Mayan Tragedy

We spent yesterday on Cozumel (Island of the Swallows), which I had always associated with Spring Break, Cancun and such. However, I did not realize the deep & tragic history the island had. Most recently, it was devastated by Hurricanes Emily and Wilma two years ago which basically flattened the island, destroyed its hotels and […]

Quantcast

Quantcast is an interesting "open internet ratings service". Much like Alexaholic is a poor man’s comscore, Quantcast provides demographic information on various websites pulled from their affiliated partners. It will give you a  quick overview, though the accuracy is going to highly variable depending upon the panels and the site.  That said, it is  interesting […]

Crowdsourcing

"You’ve got access to a global creative department of 4 billion people" — Steve Henry, Exec Creative Director at TBWA People have always said that you should listen to your customer. Well, with the advent of Web 2.0 technologies, firms are taking this advice literally. I mentioned a while ago that I expected to see […]

Blackberry Orphans

Young children around the world have seen their parents disappear from their lives in the saddest of circumstances. Perfectly normal, functioning parent have contracted severe cases of Berryitis (also known as Screensucking) and disappeared from everyday family involvement. I am certain we will be seeing TV ads to help support these poor orphaned children… My […]

A Microsoft Ass Whooping

Two key theme we discuss often here are: the importance of simplicity and transparency with customers and beware of strategics. Well… Microsoft recently launched the Zune player. It is a massacre. You have probably seen the (uniformly horrible) reviews. It could be one of the quickest tube shots (or bloodiest) in the history of consumer […]

What Sequoia Expects from Entrepreneurs

Entrepreneurs are always trying to figure out what it takes to get funded by the brand name venture groups. VCRatings recently wrote a post using Sequoia’s website criteria for what they look for in a start-up. While these seem fairly straight forward, I thought it would be helpful to expand on some points. Historically, the […]

Google Cocaine

The paid search revenue model is very addictive. New companies are launching everyday, leveraging online paid search engines to drive revenue. This obviates the need for bag carrier or other uncertain, high cost sales models. With cheap, commoditized infrastructure, any Joe and their dog can get into the online game. There has also emerged an […]

Tree Whacking

Chicago was hit by its first hard snow of the winter. American cancelled a lot of its flights from midnight through noon today and the roads are an icy mess (though starting to shape up). Our dog is in second heaven, jumping through the snow and as we shovel the walkways, thinks we are throwing […]

Chance Encounter

"Chance favors the prepared mind" — Louis Pasteur My love/hate relationship with the Economist continues here on this post. I love to read the Economist as it is, in my opinion, one of the best written (if not the best written) magazine in circulation. Because of the breadth of international topics and the density of […]

Screen Sucking

I am always curious about the various strategies people have for time management. In particular, my nemisis is anything with a screen on it. My Blackberry and Mac top the list. Like an alcoholic, I am addicted to LCD’s and the connectivity they bring me. Dr. Edward Hallowell has written a couple of books on […]

The Expert Mind

Chess has been called the "Drosophila of cognitive science" (in honor of the experimental fly) because it can be measured, broken into components, observed and modified. Much of the research in cognitive science has been around trying to understand the "Expert Mind" and whether its skills are innate or acquired. More importantly, how does the […]

The Passion For Greatness

“Research now shows that the lack of natural talent is irrelevant to great success. The Secret? Painful and demanding practice and hard work.”— Fortune Magazine Two years ago, I went down with my son to the Ledbetter Golf Academy for a father-son week. Ledbetter is part of the IMG (sports management giant) sports complex that […]

Advisory Board

While having a board of advisors makes intuitive sense, its usefulness is very hit or miss. To begin with, entrepreneurs often seek brand name individuals who, by definition, have very busy schedules. While having a deep pool of experience, often it is tied to larger corporate issues. These advisors also  don’t have much of a […]

CapiTaliTIS

It’s the weekend, so time for a more satirical look at the tech world. There is a growing outbreak in the technology world around capitalization. It is now passe for a firm to have just one capitalized letter in its name. Names are being created by combining words and each of the original words get […]

Care & Feeding of a Board part 3

Board Management:The care and feeding of a board is as much art as science. I have seen functional boards and extremely dysfunctional boards. Here are my key takeaways: 1) Open Communications Is KingToo often, CEO’s try to manage their board by managing the flow of information going to the board.  He/she makes it clear to […]

Board Governance part 2

Board composition varies dramatically between companies.  Some entrepreneurs push to add brand name executives to their boards in order to give credibility to the firm. Others load it up with friends and close acquaintances. Others add industry players or fellow entrepreneurs. I am a firm proponent of the latter. The most functional boards I have […]

Sunscreen

In my on-going tributes to inspirational graduation speeches, I am writing about a column written by Chicago Tribune writer Mary Schmich. Okay, so this is cheating since it never became a speech though she said this is what she would have said if she had ever been invited. Baz Luhrman put it to music. This […]

Board Governance part 1

A number of readers have sent me emails regarding board of directors and advisors. I would put discussions around boards into three buckets: board structure, board composition and board management. Board Structure:I highly recommend two things around structure. First, that a company go with an odd number of board members and second, that it not […]

Board Governance part 1

A number of readers have sent me emails regarding board of directors and advisors. I would put discussions around boards into three buckets: board structure, board composition and board management. Board Structure:I highly recommend two things around structure. First, that a company go with an odd number of board members and second, that it not […]

The Starfish

In the previous post, I referred to "the starfish story". Here it is. A young boy and his grandfather were walking down the beach. It was a beautiful afternoon and the tide had pulled backed leaving hundreds of starfish stranded on the sand. The boy began to run around, picking up the starfish and throwing […]

RSS Adoption

Make it simple and make it work well. This is a product development mantra that I believe strongly in. Elon Musk, Michael Moritz and others are very product centric in their view of successful tech companies. If the product works well, people will not only use it but also virally recommend it to their friends. […]

Mezzanine Momentum

A number of articles have started to appear that shine a harsh light on the mezzanine merchant bank groups like Advanced Equities. These groups specialize in raising capital for later stage venture companies. These firms have formed strong relationships with various brand name venture groups and help them raise "pre-IPO" capital for their businesses. These […]

A Stitch In Time…

A stitch in time saves nine  — old proverb Success and failure in entrepreneurial ventures ebb and flow frequently. It is not easy to differentiate between an on coming trend versus ordinary noise and fluctuation. Entrepreneurs often struggle to determine when to change course and when to let things play out. Having seen this dance […]

At What Price Glory

I recently received an email asking "do we have our priorities aligned properly".  While the email was a humor email (punchline below), the first half of it was illuminating in a more serious way. In all of our individual efforts to feel important and to be recognized (socially, in business circles, publications, in boardrooms, etc), […]

ESPN & the MVNO/Carrier Love/Hate Affair

ESPN announced that it was pulling the plug on its MVNO venture.  This is an unfortunate trend since MVNO’s are new service and application vendors best shots at getting into the market place. Since MVNO’s, by definition, are marketing oriented, they should, in theory, be more willing to integrate new apps or services. However, the […]

Will The Real YouTube Please Stand Up

Comscore just released its Top 10 Video Ratings. According to Comscore in July:Property              Unique U.S.          Streams Initiated               Streams per                                       Streamers (000)      by U.S. Users (MM)      Streamer——–              […]

Googlebase & S3

A couple of readers pinged me about Xdrive versus S3 (Amazon) and Googlebase. S3 is competitive at $0.15/GB and $0.20/GB transferred. Googlebase is free but Google crawls your info. I still haven’t gotten over the creapy experience of reading an email in Gmail (say a friends Caribbean trip) and seeing Caribbean ads served up by […]

TechCocktails

After a very successful first event, TeckCocktail, an informal and stripped-down quarterly networking event for technology professionals, will hold its second gathering Oct. 12 at the Gramercy in Lincoln Park. TechCocktail is run by Eric Olson of Feedburner and Frank Gruber, a local tech blogger and product manager with America Online. What I like about […]

FeedBurner

Nice piece in the Chicago Sun Times "Feedburner’s investors have its technology at their fingertips." It is not a common experience when investors can actually approach an investment as a customer. If this happened more often, I am certain that surprises and failure rates would go down in the business… Participate Media’s "Feedburner" post also […]

Pipeline Management

There is nothing more magical and mystifying than the fine art of pipeline management in a start-up. In many cases, a monkey throwing darts at a dart board would have more accuracy than the company’s sales team (hmmm…might have an idea there). The problem is that accurate revenue visibility drives activity across the entire company […]

Doerr On Start Ups

I came across this 1997 interview with John Doerr of Kleiner Perkins fame from Fast Company. A good read for entrepreneurs about startup teams…John Doerr’s Startup Manual Also, timely piece in VentureBeat about Doerr’s daughter’s comments on Global Warning "Dad, I’m scared and angry.  Your generation created this problem." What are we going to do […]

Dogster

"Dogster: where every dog has a webpage" I kid you not. Dogster has launched which is MySpace/Friendster for dogs and their owners. Dogs have always suffered from isolation and limited avenues to social networking. Now, they have a chance to unite and move up the food chain. Here is Wolfjohn’s profile a giant Schnauzer. He […]

Where Does Power Lie

"In conflict, be fair and generous.In governing, don’t try to control."   — Lao Tzu John Ketchum, who runs Corporate Programs at our portfolio company TicketsNow, reminded of this quote which is most relevant to yesterday’s post. Underneath all of the legal wrangling and finger pointing there lies a basic question: Where does power lie in […]

eVenturing.org: Entrepreneurial Resources

The Kauffmann Foundation is know for being the most active non-for-profit funding entrepreneurial activities, studies and projects. They have rolled out a resource site for entrepreneurs called eVenturing. This site has a collection of resources from aggregated blogs to surveys to "how to" reports on HR, marketing, finance and other core areas key to entrepreneurs. […]

Crystal Ball

"Prediction is very difficult, especially if it’s about the future."        –Nils Bohr,  Nobel laureate (yes using this one again!) Having made the error of writing about politics, I am now going to stick my neck out and make a prediction about our upcoming economy. Many would argue that the best way to […]

Bouncing Back

"When God closes a door, he opens a window" There are a mulititude of stories of entrepreneurs bouncing back from failure. However, none are as literal as Norman Stingley. Norman was a chemist for a rubber company that made "blow out preventors" for oil wells. He discovered a material and process that failed miserably in […]

Buzz: Google Coupons

"All the consumer needs to do it take 15 seconds a day to…"
    — many a dead internet start-up hoping for consumer behavior change

Consumers don’t always behave in the most efficient or logical manner. Many a start up has gone under waiting for the consumers to see the light and change their daily routine. Unfortunately, for most, people don’t like to change their routine and the best solutions involve interacting with consumers while they are doing something they are already doing. Online couponing has been one area that has always held significant promise but failed to deliver.

Doing Good: GoodSearch

Nik Rokop just forwarded on a cool link…http://www.goodsearch.com/. The site allows charities to sign-up and as members use the Good Search engine (powered by Yahoo), the charity gets money. Kinda like uPromise meets affiliate marketing. Most charities seem to be raising small amounts here (hard to change consumers behavior like what they search with), but […]

Buzz: VC Industry Restructuring

My father-in-law started in the brokerage trading business in the mid-1960’s. He showed me an industry tombstone advertisement page from 1969 that had over 50 regional and local brokerage firms, along with a handful of the growing national players (like Merrill Lynch). Today, nearly all of them are either dead or acquired and it is […]

Bootcamp: Be Careful with the ATM Card

The good times are back and the money is flowing. Angels are writing $3m checks, Hedge funds are writing $50m checks and VC is a low risk investment class again. Valuations are shooting up. For an entrepreneur, this should be a dream come true. I would argue, that if not careful, entrepreneurs are setting themselves […]

Doing Good: The New Venture Philanthropy Model

"So you say you want a revolution…"       — The Beatles In previous posts, I have discussed how entrepreneurs are making a difference in philanthropy. This approach is very similar to how venture capitalists approach early-stage investments. I also want to point out that you don’t have to be Bill Gates to get involved. […]

Doing Good: Small and Focused

On Monday, I will post my detailed breakdown of the new Venture Philanthropy model. However, one of the key elements is the importance of focusing your initial efforts very focused, small scale initiatives. Make the difference in a single (or couple of) person’s life and scale from there. Anthony Kennedy, Assoc Justice of the Supreme […]

Blog of the Week: Techcrunch

Created in 2005 by Michael Arrington, Techcrunch captures the pulse of Web 2.0. With over 85,000 subscribers (all through FeedBurner :)), it is the largest blog in its space. Michael reviews an amazingly broad array of new technologies and services before anyone else and overlays insightful commentary on top. For those of you new to […]

Blog of the Week: Techcrunch

Created in 2005 by Michael Arrington, Techcrunch captures the pulse of Web 2.0. With over 85,000 subscribers (all through FeedBurner :)), it is the largest blog in its space. Michael reviews an amazingly broad array of new technologies and services before anyone else and overlays insightful commentary on top. For those of you new to […]

Top 10 VC Blog

Many thanks to Andrew Fife for including me on his list of top 10 VC bloggers on the net. Below are the other bloggers on the list. All of them (including Andrew’s) are worth a read and have great insights into the venture and entrepreneurial worlds. Brad Feld – Mobius VenturesJeff Nolan – formerly of […]

Bootcamp: Slow Boat to China

There is a lot of press and buzz going around about the rise of the capital efficient start-up. These companies do not need venture capital and hence are free to grow their businesses unencumbered by some Stanford MBA, Mensa venture partner. Ironically, I am moderating a TiE panel this Thursday called "Capital Efficiency for Growing […]

Britney Teaches Physics

Created by several doctorial students at the University of Essex several years ago, this guide is a riot (in a nerdy kind of way).  In Britney’s Guide to Semiconductor Physics, with Ms. Spears’ help, the boys provide an useful overview and introduction to semiconductors. Just in case you had an interest this weekend… Introduction The […]

Bootcamp: Founders’ Equity

A while back, I asked for feedback from the community on potential topics of interest. One email had a host of questions around founders’ equity. I have been negligent in responding (I hope better late than never!). Great questions and ones that come up often. 1.  How should founding teams allocate equity amongst themselves?  What […]

Buzz: Are Acquisitions Replacing IPO’s

Tim Draper and Brad Feld have a variety of interesting observations in a recent Always On panel. One of the topics discussed is about the IPO/acquisition exit mix. Historically, this number has been around 20-25% IPO and 75-80% acquisition. Today, IPO’s make up less than 10% and dropping (and this includes overseas IPO’s). Tepid markets, […]

Bootcamp: Strategic Investors

I was talking with a friend of mine, Patrick Dealy, who is at MaxMD about the pro’s and con’s of taking strategic money. MaxMD has an interesting business model, based upon their being the primary registrar for the .MD domain extension. Doctors and medical institutions can register for www.drname.md there while also beginning to sell […]

Bootcamp: Family Life and Entrepreneurship

Balancing work and family is one of the greatest challenges for an entrepreneur. Left unchecked, your business can consume every waking hour. There are always sudden firedrills, new customer pitches or urgent personnel matters. How do you balance everything? I will be introducing a future feature called "Behind the Firewall". It will be a series […]

Our Tipping Point

"The best way to understand the dramatic transformation…is to think of them as epidemics. Ideas and products and messages and behaviors spread just like viruses do."                                     — Malcolm Gladwell We, in the entrepreneurial world, live or die based upon Tipping Points. Al Gore […]

Resilience: Steve Jobs on the Power of Failure

""Nior dhun Dia doras riamhnar oscail Se ceann eile" (God never closes one door without opening another)                                    — Irish Saying I have often written about the importance of Resilience in entrepreneurship. As they say, what doesn’t kill you, makes you stronger. This is easy […]

Resilience: Steve Jobs on the Power of Failure

""Nior dhun Dia doras riamhnar oscail Se ceann eile" (God never closes one door without opening another)                                    — Irish Saying I have often written about the importance of Resilience in entrepreneurship. As they say, what doesn’t kill you, makes you stronger. This is easy […]

Top Entrepreneurial Euphemisms

About six weeks ago, I posted on 10 VC Euphemisms and had intended to post Guy Kawasaki’s corresponding Top Ten "Euphemisms" of Entrepreneurs. This slipped by mind until Steve Vivian from Prism Capital reminded me about it. It is hilarious yet should be taken seriously. I highly recommend you not fall victim to these claims. […]

Is Your AIM True?

In 1995, the London Stock Exchange launched the Alternative Investments Market (AIM) to offer smaller firms a less regulated market upon which to float their shares. While initially viewed by many as a novelty, it has begun to gain scale and respectability as more and more international firms are using it for going public. While […]

Glory Road: Peapod

Technology revolutions always have a boom-bust-rebirth-boom pattern. The key to this is surviving the down draft when it hits. Mary Meeker, whose career has taken a similar path, laid this out in a very powerful way. She aggregated the market caps of Google+Yahoo!+eBay+Yahoo!Japan+Amazon over time.    Pre-2000 IPO           = $2B    3/2000 […]

Invasion

If you work for one of the TV networks (or even the cable guys), you are about to have a really unenjoyable two months coming up. We are entering into the upfront ad sales season for TV and for the first time, internet advertising and, increasingly, IPTV are making things uncomfortable for the networks. Advertisers […]

Chicago On The Rise

As I have been saying for some time, the Midwest is ripe for a tech rebirth. The technology is here and the customers are here. Technology is commoditizing and inexpensive, but domain/industry expertise is worth its weight in gold. The key is finding the right entrepreneurs to lead the charge (they are here, just hiding […]

Really Small Stuff

I have threatened to write a piece on the emerging importance of quantum physics. As scale shrinks down to the nano level in field after field, results are impacted by sub-atomic level interactions (quantum level) versus traditional Newtonian Physics (force, gravity,etc). While there remain considerable unknowns in Quantum Physics, there are also significant opportunities from […]

Really Small Stuff

I have threatened to write a piece on the emerging importance of quantum physics. As scale shrinks down to the nano level in field after field, results are impacted by sub-atomic level interactions (quantum level) versus traditional Newtonian Physics (force, gravity,etc). While there remain considerable unknowns in Quantum Physics, there are also significant opportunities from […]

Private Equity & its Economic Role

On Friday, UoC and UoI hosted their annual Private Equity Conference. Steve Kaplan, the primary organizer from UoC, did a masterful job pulling together quite a few interesting panels with panelists from leading universities such as UoC, Northwestern, UoI and Berkeley as well as numerous participants from the general partner ranks. Topics included:— Agency costs […]

Private Equity & its Economic Role

On Friday, UoC and UoI hosted their annual Private Equity Conference. Steve Kaplan, the primary organizer from UoC, did a masterful job pulling together quite a few interesting panels with panelists from leading universities such as UoC, Northwestern, UoI and Berkeley as well as numerous participants from the general partner ranks. Topics included:— Agency costs […]

Leisure Class

If one is to believe that a country’s long-term prosperity and growth is tied to the strength of its innovation and science, the US is in increasing trouble. I fear that we will not begin to take things seriously until we are fairly down the declining path. Marc Faber presented two interesting tables from Robert […]

Resilience In The Storm

(Originally published 2006 in VC Confidential) Resilience is a key theme you will hear about time and time again in the entrepreneurial world. The ability to persevere and bounce back from adversity is part of the DNA of a successful entrepreneur (and VC Sith Lord). During the 1999-2002 period, nearly everyone in the venture and […]

The Black Art of Deal Pricing

Summary:— pricing is driven off of multiples not IRR— VC’s target 10x due to high failure rates— start at the expected final valuation and work backwards. What area of venture capital is more opaque and mysterious than how VC’s price deals? Professors have tried to quantify and analyze what we do. Ironically, it is quite […]

World Is Flat part II

In yet another indication of how global the entrepreneurial world is becoming, our portfolio company, Imago, just acquired its primary competitor, an English company, while selling nearly half of its machines in Asia and Europe. Imago sells a mulit-million dollar 3-D atomic probe (atomic microscope).  (Congratulations Tim & team!) Following up on yesterday’s post, when […]

World Is Flat

Here is another supporting fact about our how flat our world truly has become. I use Blogbeat (thanks to Brad Feld’s suggestion) to analyze site traffic. Here is the "City Cloud", listing where visitors to my site came from since last night at Midnight until 8am today (the bigger the letter, the more traffic from […]

Affluenza Outbreak

Scott Burkett and I have been blogging back and forth about the importance of giving back, the power of small groups and the need for philanthropy. His most recent post, Philanthropic Entrepreneurship: Up Close talks about an entrepreneur in Atlanta, Tom Flaim, and his brother who started a not-for-profit company, First Wate Systems, to provide […]

Jobs/Wozniak Setbacks and other Stories

My wife just bought a book for our kids by Steve Young (the motivational guy, not the quarterback) titled "Great Failures of the Extremely Successful". It is a mixture of inspirational quotes, short snippets and essays from famous people who have overcome adversity. For entrepreneurs dealing with the day to day challenges and setbacks of […]

Horse or Jockey?

There is much discussion in the venture business about whether you back the horse or the jockey. Some, like Don Valentine at Sequoia, state they look for large growing markets and find the team later. More frequently, you hear VC’s saying that the business is about people, people, people.  In the end, I would argue […]

Top VC Euphemisms

Guys Kawasaki, Apple’s famed ex-evangelist, is well known for his top 10 lists. He published his Top Ten VC Lies earlier this year.  There is no such thing as "No" in the VC business, just indefinite "Maybe’s". While somewhat tongue and cheek, these should help shed some light on interpreting VC talk. The Top Ten […]

The Truth Will Set You Free…Maybe

Corporate America has a love/hate relationship with the freedoms created by the various Web 2.0 technologies like blogs.  At the Blog-On conference last Fall, I noticed the audience broke into three sections. You had the corporate communications and PR teams, the technology providers (blog services, business intelligence/analytics, etc) and the revolutionaries. The corporations expressed an […]

Entrepreneurial Proverbs

Tim Draper recently sent me this great post from Marc Hedlund at O’Reilly on Entrepreneurial Proverbs.   Lot of great advice summarized here (including from Chicago’s own Jason Fried). Starting It’s good to be king — being an entrepreneur is the best job I’ve had. Every day your job is new and different; you constantly have […]

Entrepreneurial Proverbs

Tim Draper recently sent me this great post from Marc Hedlund at O’Reilly on Entrepreneurial Proverbs.   Lot of great advice summarized here (including from Chicago’s own Jason Fried). Starting It’s good to be king — being an entrepreneur is the best job I’ve had. Every day your job is new and different; you constantly have […]

Pandora’s Box

Search on the web is in a lot of pain right now. Content, including enormous amounts of user generated videos, audio files and test, is exploding at an exponential rate. There are over 31 millions blogs, including this one, growing at 70,000 per day. I don’t know about any of you, but I have grown […]

Emmanuel’s Gift

Jim Clark once said that great companies are not built, but rather willed into existence. Clark knows a few things about this, as he is the co-founder of Silicon Graphics, Netscape, myCFO and Healtheon/WebMD. Progress is never linear, and often, successful companies flirt with death before grabbing the golden ring. AOL nearly went under on […]

TrustID: You Can Trust Us

Michael Arrington wrote a great piece in Techcrunch on one of the latest additions to our portfolio network, TrustID. Their newest service, IDFreeze, is targeted at protecting consumers from the growing issue of identity theft. I recently became a customer ($7.95/mo) and will report back on the experience. As Michael writes:"TrustedID launched their first product, […]

Buffett on The Investor/Entrepreneur Dance

What is the right role for an investor with a portfolio company? When VC’s make an investment in a company, the founder/entrepreneur is often concerned about what impact his/her new partner will have on issues like control, degrees of freedom to operate, core decision making and future employment. There are many stories of VC’s swinging […]

World on Fire

World on Fire This posting is part philanthropy, part tech. I came across a wonderful music video the other day on Veoh from Sarah McLachlan about her top 10 song, World on Fire. In it, she shows the impact that relatively small amounts of money have on the hundreds of millions of people in poor […]