Why Your Software Buyer and Sponsor Might Prefer a Multi-Year Contract
The normal discussion with software sales teams is all around creating special incentives for these teams to sell multi-year contracts instead of settling for annually renewable contracts. Multi-year deals are viewed as harder to sell and less likely to close and sales teams are looking for as fast and as certain a win as possible. […]
Full ArticleEntrepreneurial Optimism Versus Fraud
Everyone talks about an entrepreneurial culture of “Fake it until you Make It” and how things can go wrong if this is taken too far. The instances of fraud in venture investments goes well beyond what has been alleged at Theranos and Ozy. Pick a vibrant venture ecosystem and there will be stories with some […]
Full ArticleWhat Should Software Start-up CEOs Be Thinking About As Inflation Risk Rises
Two of my kids are studying economics as part of their majors or areas of concentration and in the past couple of weeks, each has raised the issue of inflation with me. Inflation seems to be a front and center topic in university economic departments these days and probably with good reason. I am not […]
Full ArticleInvesting in a Time of Near Complete Uncertainty
People have begun speaking about the new normal that will exist after the Covid-19 period subsides and how many things will change – how will we recover and take care of the people affected directly and indirectly, how we will work, how we will educate, how medicine will be delivered, how much we will or […]
Full ArticleBroad Option Distribution? No Debate – the Answer is Yes!
There is a debate that often happens among investors, management, and other board members about the value of options for non-executive employees in start-ups. Sometimes investors worry about the dilutive effect and ask the question. Other times it is founders who see the impact of additional refreshes of the option pool on their ownership. I […]
Full ArticleRethinking Venture Debt During Periods of Economic Headwinds
I began my career at Chemical Bank (now JPMC) in New York and spent my first year going through the well-regarded credit training program. It was not too long after the early 1980s and people still remembered high inflation and high interest rates. We were trained to run financial projections on the ability of a […]
Full ArticleThe Winding Down of Venture Investments
A certain percentage of companies that venture funds back fail. Everyone knows this. Depending on their investment strategy and success, funds lose most of their capital on 25% to 50% of portfolio companies. Of these, some percent are sold for very little value, but the sale provides a home for the technology, the customers, and […]
Full ArticleTurning Over Another Card Is for Poker, Not Technology Investing
I was with a co-investor recently and we were discussing our mutual investment. It is a situation where we have been frustrated with progress, both in terms of developing a scalable product and in getting early customer traction (these are certainly correlated). My colleague made the statement that if one thing or another happened, he […]
Full ArticleThe Compounding Effect of a CEO’s Day-to-Day Decisions
A colleague of mine recently stepped away from his day-to-day role as a partner in a venture fund and into an interim six-month role as Executive Chair in one of our portfolio companies. It was a necessary move to stabilize what will likely be a very good company and it was a great move for […]
Full ArticleThe Fallacy of the Messiah Hire
“There is no Messiah in here! There’s a mess alright, but no Messiah.” A memorable line spoken by Brian’s mother in Monty Python’s Life of Brian. The truth is, I often think of this line when CEOs speak to me of the person they just hired or the new person who just started. It is always […]
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