When the VC-Entrepreneur Honeymoon Ends

Sep 30

In: Entrepreneurship, Technology and VC

Eric and I have been on quite a few boards. That’s another way of saying that we’re in our 40s, which qualifies as “old age” in today’s hip and young entrepreneurial world.

But, with age, hopefully, comes self-awareness.

For example, one thing for which we are prepared is when the honeymoon period with a founder ends. Here’s a typical dynamic between a VC and an entrepreneur:

  • Entrepreneur is in “sell mode” and pitches the VC–and, it goes really well
  • VC accelerates his/her diligence process and pushes to a partners’ meeting. They love the company and move to “sell mode”
  • Terms are agreed to and the money is wired. Some good dinners and wine are shared convivially sometime during this process
  • Board meetings start. Over time, the burn rate goes up as new hires are made, offices are furnished and gear is purchased. Over time, progress is slower than promised in the original business plan
  • Over time, tension rises at the board meeting. The VC’s partners are wondering why progress is slow. Does the market suck? Does the entrepreneur suck? Does our fellow VC suck?
  • Over time, stress reveals the entrepreneur’s relative weaknesses. It might be a skill-set gap, or a style quirk. Same for the VC
  • Tensions continue to rise. Trust erodes. Eventually, there’s a sharp exchange of words

In my experience, it is usually the case that the honeymoon ends. The intentions were all good, but because each side was in “sell mode” at the beginning of the partnership, a new reality often sets in, and it isn’t pretty.

That’s why we often talk internally about:

  • Be aware if we’re in a honeymoon period with the entrepreneur. Know when the honeymoon has ended
  • We’ll learn about the entrepreneur’s glaring weaknesses over time
  • An entrepreneur’s greatest strength usually translates to his/her greatest weakness. You have to accept both manifestations, as a VC
  • One of our jobs is to help source recruits who can complement the entrepreneur’s strengths and weaknesses

I’ve found that by being mindful of all this, it really helps immunize me from the ups and downs of our companies’ journeys. Not always, but usually.

And, it helps clarify our role: as I’ve blogged previously (here), our job is to help the entrepreneur succeed. Firing founders never works, IMO. You have to build a team that complements them.

My Top 5 Personal Possessions

Sep 27

In: Personal, Philosophy


It is Saturday morning, and I just went shopping. We are looking for new kitchen appliances.

Honestly, I changed my game plan when I got to the appliance store. My original plan was to do pretty intense due diligence and stack rank all the appliances based on features, price and quality. When I arrived, however, my heart just wasn’t in it.

There’s a dizzying plethora of appliances. Take ovens, for instance. Gas, electric or dual fuel? Integrated with a cook top or separate? 30″ width, 36″, or wider? It goes on and on. Then, similar choices for dishwashers, microwaves, and refrigerators.

I realized that I could spend hours on this stuff. But, the appliances eventually will break, get scratched up, and become obsolete. The phrase “diminishing returns” kept popping into my head, meaning I could spend five hours on this shopping excursion or just one.

Also, I started to think about how fleeting material goods are. I remembered how pumped I was to buy a BMW 5-Series, and how bummed I was when I scratched a bumper one week in.

Then, this will sound weird, but I also started thinking about a parent at one of my children’s schools. I don’t know who she is by name. She is a victim of domestic abuse and is now a recluse. Her ex-husband disfigured her face, and she now never leaves her home.

Spending hours on appliances just didn’t feel right. So, I made my selections in 45 minutes and left.

I kept thinking about material goods as I went a few blocks away to grab a bowl of bún bò Huế at Pho Le (photo up top). That bowl of noodle soup was simple but so very awesome. It cost a fraction of what the cheapest appliance at the store cost.

This made me think that, no matter how much or how little money you have, the essentials in life are actually very few. There are many wants but very few needs. I decided to “boil down” my list of possessions. What are the true essentials in my life?

So, a list of my top 5 possessions is below. I’ve excluded “shared” possessions, such as our house. I’ve also excluded intangibles, such as my health and relationships with family and friends. I also excluded money, since I’m viewing it as an enabler of possessions.

Jo’s Top 5 Personal Possessions

1. Smart phone

2. Fly fishing equipment

3. Gym membership

4. A decent and very basic wardrobe

5. A reliable car

I noticed that limiting the list to just five items made me exclude a number of things:

  • My iPad (my iPhone will be enough)
  • My laptop (I rarely use it now anyways)
  • My skis (I’d pick fly fishing over that if I had to)
  • Red Sox season tickets (sad to say, but true: not in the top 5)
  • My non-digital books and magazines (I can read them on an iPhone)
  • Oodles of stuff in my closet and in our basement

This was an exercise worth doing. I was stunned as to how easy it was to pick five possessions. Appliances aren’t on my list. And, I was struck by how few personal possessions I truly need beyond the basics.

Now, what are your Top 5 personal possessions?

Catching Tiger Trout

Sep 21

In: Fly fishing, Personal

What a great day!

I went fly fishing today on Sunday. I awoke at 3.30 am to drive to the river. I’m grateful to my family for giving me a hall pass.

The water was super-low but the the trout were decently active now that temperatures have dropped here in New England. Many trees along the river have started to display their pink/orange/yellow autumn colors, and there was a brisk breeze and a bit of rain in the morning.

I only saw one other angler and it felt as though I had the whole river to myself. I fished in a rural area, in a canyon. It’s a protected wildlife area and incredibly beautiful. The only sounds you hear all day are the gurgling of the river, the occasional bird, and if I’m lucky, the splashing noises of trout slurping insects from the surface.

I really like fly fishing. The more I learn about it, the more I realize there’s more to learn. I’ve been incorporating new techniques this past summer, and I just recently started fly tying.

The biggest fish today was a very large tiger trout, its fat belly a blazing orange color. I didn’t take a picture, but above, is what it looked like.

A great way to spend the first day of autumn.

‘Damsels in Distress’

Sep 18

In: Fly fishing, Personal, Politics

I don’t know about you, but the thought of our nation re-engaging in Iraq has me torn. It’s clear that something has to be done to stop the horrific killings of children, but I don’t think air strikes will be enough. I’m also of the mind that our soldiers have already paid a huge price on the ground there.

So, I wanted to lighten up your mood, and mine, and share a cool nature video. If you like the outdoors and/or fishing, the video is above (or, click here). It is called “Damsels in Distress.” A storm prevented some fly fishermen from fishing. Instead, they stumbled upon, and then filmed, a wonderful scene.

Truly incredible footage and the case of good stuff coming from a disappointing outing. We’re supposed to make lemonade out of lemons. That video there is some amazing lemonade.

A Good Evening with NEVCA

Sep 16

In: Entrepreneurship, Personal



I had a good time last night at my last New England Venture Capital Association (NEVCA) Board gathering.

I ran into some prior colleagues, and it was great to see them (fun to catch up with you, Dan, Bob and Sean). I also had a chance to meet up again with C.A. Webb and Kitt George, who run the group, as well as the many VCs and entrepreneurs on the Board. Plus, they gave to me a cool fleece with the group’s logo (see above).

I think volunteer work is often a mixed bag. Decision-making can happen at a slow pace, although intentions are nearly always good. That has not been the case with the NEVCA Board. I really like how the group focused on impact and positive change. There was a sense of urgency.

I feel that I helped accomplished some things. Will miss working with C.A. and Kitt, though. I’ve always wanted younger sisters, and it has been a privilege to hang with them.