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Browse: Home / lessons learned

lessons learned

Unicorpse and The Moral Hazard of Making Unicorns

Unicorpse and The Moral Hazard of Making Unicorns

By Derek Pilling on January 8, 2016

I’m sure that many more thoughtful than me has written about the moral hazard of venture capital. In economics, moral hazard occurs when one person takes an unreasonable risk because someone else will bear the burden of the negative consequences. In the age of unicorns, the moral hazard in venture capital has never been greater. Moral hazard […]

Posted in Business, Featured Posts | Tagged Company Building, Entrepreneuriship, Growth Equity, lessons learned, moral hazard, Raising Capital, unicorn, unicorpse, venture capital

We Sell the Ultimate Commodity – Money

We Sell the Ultimate Commodity – Money

By Derek Pilling on May 1, 2014

Last month I participated in a panel discussion at Denver University organized by Maclyn (Mac) Clouse. Mac is a long-time educator and supporter Denver’s entrepreneurial community. I was joined by Peter Adams, Executive Director of the Rockies Venture Club. Mac’s setup for the discussion was “dangerous” because he offered both Peter and I the opportunity […]

Posted in Business, Entrepreneurship, Featured Posts | Tagged DU Finance Forum, Growth Equity, lessons learned, Mac Clouse, Peter Adams, Raising Capital, restrictive covenants, Rockies Venture Club, value-add, venture capital

Improv at the Office: Yes, and…

Improv at the Office: Yes, and…

By Derek Pilling on March 19, 2014

When I get really busy, I communicate less effectively. Truth is, I don’t listen as well, I get short in my responses and I cut off conversation prematurely, because I’m so focused on getting onto the next thing. I’m not proud of it, but it happens. The First Rule of Improv When I was in […]

Posted in Entrepreneurship, Featured Posts | Tagged and, business communication, communication, improv, lessons learned, yes

Finding harmony between advice and self-interest

Finding harmony between advice and self-interest

By Derek Pilling on January 31, 2014

I just wrapped one of those calls where I had the opportunity to give advice to an entrepreneur that runs counter to my short-term interests. In this case, it is a story of a first-time entrepreneur who has built a $7 million revenue business and is wrestling with the decision whether to take growth capital […]

Posted in Entrepreneurship | Tagged Entrepreneur, exit, Growth Equity, lessons learned | 1 Response

What is an entrepreneur to do when restrictive covenants become restrictive

What is an entrepreneur to do when restrictive covenants become restrictive

By Derek Pilling on January 27, 2014

Restrictive covenants are standard features of venture capital, growth equity and private equity transactions although each investor type has its own standards. Restrictive covenants are the actions a company cannot take without investor approval. A short list of typical restrictive covenants includes: A sale of a Company or sale of a majority of the Company’s […]

Posted in Entrepreneurship, Featured Posts | Tagged Growth Equity, lessons learned, restrictive covenants, venture capital, Working with Invesors

What Entrepreneurs Can Learn From Peyton Manning

What Entrepreneurs Can Learn From Peyton Manning

By Derek Pilling on January 24, 2014

I’m not a huge football fan. But I do marvel at the drama of professional football. In particular, I admire what Peyton Manning has done for the Broncos the past two years. His individual contributions are well documented. But what I’ve been most impressed by is the positive impact he seems to have had on the […]

Posted in Entrepreneurship, Featured Posts | Tagged contingency planning, execution precision, greatness, leadership, lessons learned, Peyton Manning, Random, selflessness, urgency, work ethic

The fallacy of averages

The fallacy of averages

By Derek Pilling on January 23, 2014

A discussion with a portfolio company CFO  reminded me that statistics are a dangerous thing and averages are misleading. “There are three types of lies — lies, damn lies, and statistics.” Most businesses analyze their performance using overly simplistic tools. For an extreme example, imagine a scenario where the average customer produces monthly recurring revenue […]

Posted in Business | Tagged average, decision-making, histogram, lessons learned, mean, median, statistics

You missed your numbers. Now what?

You missed your numbers. Now what?

By Derek Pilling on January 20, 2014

By now, you should know where you stand relative to your 2013 budget. Hopefully, you made it or beat it. For some, the finally tally will show a “miss to the downside”. When i say miss, I’m referring to performance against the original budget – the one you put together in December 2012. Performance against […]

Posted in Business, Featured Posts | Tagged Budgeting, Execution error, Forecasting, lessons learned

Image credit: GigaOM

One Surefire Way to Screw up Your Lifestyle Business

By Derek Pilling on September 2, 2011

Some businesses are designed – maybe even destined – to be owner operated. Industry parlance often refers to these businesses as lifestyle businesses. Wikipedia has a nice definition. They are typically small, profitable, generate cash and enable their owner-operator to sustain a well-above average lifestyle. In some circumstances, they may even make their owner-operator filthy […]

Posted in Entrepreneurship | Tagged Entrepreneur, Growth Equity, Investment Selection, Investor, lessons learned, lifestyle business, Raising Capital

Implementing Enterprise 2.0 at Intuit, Part Five: Operational Impact and Lessons Learned

Implementing Enterprise 2.0 at Intuit, Part Five: Operational Impact and Lessons Learned

By Jacob Morgan on July 26, 2010

This is part five (and the final part) in a multi-part series on how Intuit is implementing Enterprise 2.0 within their organization.  Part one covered the business drivers of Enterprise 2.0, part two looked at some of the change management issues of Enterprise 2.0, part three explored cultural and organization shifts,  part 4 talked about […]

Posted in Enterprise | Tagged case studies, collaboration, e2.0 case study, enterprise 2.0, Enterprise 2.0 case studies, intuit, lessons learned, operational impact | 5 Responses

Why I’m Contrary on Compensation

By Derek Pilling on June 28, 2010

When I was a teenager, I spent two summers working in a furniture manufacturing factory. The company, Steelcase, was (and still is) one of the largest office furniture manufacturers in the world. I worked in the binder-bin plant – a binder-bin is the cabinet that mounts on the back of your desk at about eye-level. […]

Posted in General | Tagged books, compensation, Daniel Pink, Drive, Economics, Edwards Deming, lessons learned, punishment, rewards, The New Economics, venture capital

Implementing Enterprise 2.0 at Océ Part Five: Lessons Learned and Future Plans

Implementing Enterprise 2.0 at Océ Part Five: Lessons Learned and Future Plans

By Jacob Morgan on May 10, 2010

This is part five (and the final part) in a multi-part series on how Océ is implementing Enterprise 2.0 within their organization.   Part one covered the Business Drivers of Enterprise 2.0, part two covered Making the Push for Enterprise 2.0 ,  part three covered Change Management for Enterprise 2.0,  part four covered the Operational […]

Posted in Enterprise | Tagged case studies, case study, e2.0, enterprise 2.0, Enterprise 2.0 case studies, future plans, lessons learned, oce | 1 Response

What is this “Momentum” of Which You Speak?

What is this “Momentum” of Which You Speak?

By Derek Pilling on November 18, 2009

A meeting with an entrepreneur last Friday reminded me of the most frustrating and overused feedback entrepreneurs receive from VCs: Talk to me when you have “momentum”; or I need to see some “traction” first. With more and more VCs looking to make later stage investments, entrepreneurs are receiving this feedback more than ever. You can […]

Posted in Entrepreneurship | Tagged Entrepreneur, growth capital, lessons learned, markets, startups, value creation, venture capital | 2 Responses

Managing your Board; Give ‘em a job!

By Derek Pilling on November 11, 2009

In a post last week, I addressed the notion that everyone needs someone to report to. After all, you can’t report to yourself.  The reporting relationship between a CEO and a Board is critical for a Company’s success. That relationship must be based on trust, candor, and transparency. While that hierarchical reporting relationship is necessary and […]

Posted in Entrepreneurship | Tagged Boards, Entrepreneurship, governance, lessons learned, reporting, startups, venture capital | 1 Response

The math of SaaS revenue growth

By Derek Pilling on November 10, 2009

A conversation with the CEO of a SaaS company today reminded me of the importance of the rule of 78s. What is this “rule”, you ask. If you run a recurring revenue business, it is the most important number you have never heard of. Back to my conversation with the CEO. We were talking about the […]

Posted in Analysis | Tagged Economics, lessons learned, recurring revenue, rule of 78, saas, Uncategorized, venture capital | 4 Responses

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