Category

Entrepreneurship

Blogiversary, Part VII

Blogiversary, Part VII Today marks the seventh anniversary of OnlyOnce.  I haven’t marked the date with a post in three years, but here was my last such post (with links to prior posts in it).  In sum up until now, my reasons for blogging have been written up as: “Thinking” (writing short posts helps me crystallize my thinking) “Employees” (one of our senior people once called reading OnlyOnce “getting a peek inside Matt’s head) My book reviews help me crystallize my takeaways from books and serve as a bit of a personal reference library I like writing and don’t get to do it often After seven years, though, I’m going to add another important point of value for me for…

Why Winning Matters (Especially When You’re Young)

The Direct Marketing Association (DMA) has long been a leading voice for direct marketing for nearly 100 years – back when direct marketing was really only about postal. It has evolved in that time to include phone, fax (for the nanosecond that was relevant), and then interactive tactics, including email. While the DMA has not always incorporated the new technologies in the most elegant way – the tendency has been to apply previous best practices, even when consumers have demanded a new way of thinking – the organization has made tremendous strides in recent years to re-shape itself into an organization that will be relevant for another 100 years. And one way it is doing that is by supporting and…

First Rate Intelligence

First Rate Intelligence One of my favorite quotes of all time comes from F. Scott Fitzgerald, as he wrote in 1936 in “The Crack Up” (which you can read here in Esquire): The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function. Before seeing this article recently, though, I’m not sure I’d ever seen the sentence that follows: One should, for example, be able to see that things are hopeless and yet be determined to make them otherwise. I’ve talked about the Highs and Lows of being an entrepreneur a couple times in the past — here as it relates to the…

Guest Post: Staying Innovative as Your Business Grows (Part Two)

As I mentioned in a previous post, I write a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. I share the column with my colleagues Jack Sinclair and George Bilbrey and we cover how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. I recently posted George’s column on Staying Innovative as Your Business Grows (Part One). Below is a re-post of George’s second part of that column from this week, which I think my OnlyOnce readers will enjoy. Guest Post: Staying…

Backwards

Backwards I came to an interesting conclusion about Return Path recently.  We’re building our business backwards, at least according to what I have observed over time as the natural course of events for a startup.  Here are a few examples of what I mean by that. Most companies build organically for years…then start acquiring others.  We’ve done it backwards.  In the first 9 years of our company’s life, we acquired 8 other businesses (SmartBounce, Veripost, Re-Route, NetCreations, Assurance Systems, GasPedal Consulting, Bonded Sender, Habeas).  Since then, we’ve acquired none.  There are a bunch of reasons why we front loaded M&A:  we were working hard to morph our business model to achieve maximum success during the first internet downturn, we knew…

The Fear/Greed Continuum

The Fear/Greed Continuum My old boss from a prior job used to say that every buyer (perhaps every human in general) could be placed at any point in time somewhere on the “fear/greed continuum” of motivation, meaning that you could win him or her over by appealing to the appropriate mix of those two driving forces if you could only figure out where the person sat on the spectrum.  I’ve found this to be true in life, more in selling situations than anything else, but probably in any negotiation. Think about some examples: Is your product an ROI sale (you’re appealing to greed), or do all your prospect’s larger competitors use you (fear they’ll get fired if they don’t adopt)?…

Should You Have a Board?

Should You Have a Board? As I mentioned last week, Fred’s post from a few months ago about an M&A Case study involving WhatCounts had a couple of provocative thoughts in it from CEO David Geller.  The second one I wanted to address is whether or not you should have take on institutional investors and have a Board.  As David said in the post: Fewer outsiders dictating (or strongly suggesting) direction means that you will be able to pursue your goals more closely and with less friction Although I have a lot of respect for David, I disagree with the notion that outsiders around the Board table is inherently bad for a business, or at least that the friction from…

Size of Pie, a.k.a. What Type of Entrepreneur Are You?

Size of Pie, a.k.a. What Type of Entrepreneur Are You? Mmmm…pie.  A post that Fred had up a few weeks ago about an M&A Case study involving WhatCounts, a company in the email space that I’ve known and had a lot of respect for for years, got me thinking about two different topics.  The first is thinking about types of entrepreneurs.  I’ve always said there were two types:  serial entrepreneurs who are great at starting companies but less great at scaling them, and entrepreneurs who are often part of a group of founders but who go on to continue to run the business for the long-haul. CEO David Geller’s quote that gets to the heart of this in Fred’s post…

Connecting with Other CEOs

Connecting with Other CEOs CEOs get introduced to each other regularly.  Sometimes it’s through VCs or other investors, sometimes it’s through other CEOs, sometimes it’s because the two companies are already partners.  I try hard to meet personally or at least on the phone with other CEOs every time I get a chance, sometimes because there’s business to be done between Return Path and the other company; but always because I come away from every interaction I have with another CEO with some learnings to apply to myself and the company. I have noticed two unrelated things over the years about my interactions with other CEOs who are in our industry, and therefore with whom I spend time more than…

Guest Post: Staying Innovative as Your Business Grows (Part One)

As I mentioned in a previous post, I’ve recently started writing a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. I share the column with my colleagues Jack Sinclair and George Bilbrey and we cover how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. Below is a re-post of George’s column from this week, which I think my OnlyOnce readers will enjoy. Guest Post: Staying Innovative as Your Business Grows (Part One) By George Bilbrey As part of The Magill Report’s…

The Art of the Post-Mortem

The Art of the Post-Mortem It has a bunch of names — the After-Action Review, the Critical Incident Review, the plain old Post-Mortem — but whatever you call it, it’s an absolute management best practice to follow when something has gone wrong. We just came out of one relating to last fall’s well document phishing attack, and boy was it productive and cathartic. In this case, our general takeaway was that our response went reasonably well, but we could have been more prepared or done more up front to prevent it from happening in the first place.  We derived some fantastic learnings from the Post-Mortem, and true to our culture, it was full of finger-pointing at oneself, not at others,…