Nate Lentz
October 11, 2022

Can You Recession-Proof Your Customers?

“Enterprise sales processes are slowing and some deals that feel like they were won are not getting across finish lines because of CFO mandates on no new spend.” At Osage Venture Partners, we are already hearing these rumblings.  Not everywhere and not at every portfolio company, but enough to see that spending sensitivity is beginning […]

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Nate Lentz
November 3, 2021

“Big Brain” Software Platforms versus “Small Brain” Best-of-Breed Applications

I recently got asked if I thought there was going to be a future need or demand for proprietary software platforms or if the evolution of APIs and the ability to efficiently connect best-of-breed applications would render the concept of a platform a thing of the past.  It is a good question.  As data easily […]

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Nate Lentz
October 18, 2021

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.  […]

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Nate Lentz
October 14, 2021

Entrepreneurial 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 […]

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Nate Lentz
May 3, 2021

What 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 […]

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Nate Lentz
January 13, 2021

Don’t Under-rate the Impact of Leadership – Let FDR Be an Example for Biden, Congress, and the Rest of Us in Stemming the COVID Tide

Franklin Roosevelt is a perfect example of the kind of leaders we need in the country today.  I have been listening to Doris Kearns Goodwin’s Leadership in Turbulent Times and her Chapter on Turnaround Leadership – Franklin Roosevelt and the Hundred Days could not be more timely for what faces our country over the coming […]

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Nate Lentz
September 2, 2020

Recording Zoom Meetings or “Play It Again, Sam!”

In this current environment of sheltering in place and virtual meetings, everyone in the investment community is well aware of the challenges of not meeting with people face-to-face.   It takes longer for personal connections to be created.  There are fewer sidebars and casual interactions where we traditionally begin to feel comfortable with people.   Non-verbal clues […]

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Nate Lentz
July 14, 2020

Most of our Portfolio CEOs Say “See You at The Office in 2021”

We recently held a zoom conference with our CEOs to discuss reopening the office and to share what people were learning, thinking, and how they were preparing.  100% of participants are business-to-business software start-ups and almost 100% of employees are college educated with salaries averaging above $100k, so their perspectives will be very different from […]

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Nate Lentz
May 12, 2020

Watch Out for the Next Gray Rhino – Beware the Coordinated Cyber-Attack

In this time of COVID-19, many people have used the term “Black Swan” to describe the pandemic and its global and national impact. But “Black Swans” are defined as “Events that are highly improbable, difficult to predict, and have massive impact.” Our current situation has had massive impact, but it certainly wasn’t improbable or difficult […]

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Nate Lentz
April 2, 2020

Investing 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 […]

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