That Didn’t Need To Take An Hour

Have you ever finished something and thought to yourself, “That didn’t need to take an hour?”

In my world, I have an endless stream of requests to do something for an hour. I just looked at my calendar for the next two weeks and almost everything that someone else scheduled and invited me to is for an hour.

In contrast, all of the things I (or my assistant) have scheduled are for 30 minutes. And many of them will take five minutes.

If you schedule a meeting for an hour, it’s remarkable to me how often it takes an hour, even when it doesn’t need to. Three hour board meetings, especially when board members have traveled to them, take – wait for the drum roll – three hours.

During the day, between Monday and Friday, I generally have a very scheduled life. I go through phases where I shift into Maker Mode, now no longer schedule anything before 11am my time (with occasional exceptions), and try to have a very unscheduled weekend. But Monday to Friday looks like the following:

This Week - A Normal One

Over time, I’ve come up with some approaches to deal with this massively over-scheduled life in order to stay sane. Here are a few of them.

30 minute schedule slots: I’ve tried it all. 60 minutes. 15 minutes. 5 minutes. 45 minutes. 37 minutes. The only thing that I’ve found that works is 30 minutes. If I schedule for 15 minutes, I inevitably have too many things in a day and get completely exhausted. If I schedule for more than 30 minutes, I find myself twiddling my thumbs and trying to get finished with the meeting. 30 minutes seems to be the ideal amount to get any type of meeting done.

A walk: If I have a longer, more thoughtful discussion I want to have with someone, I go for a walk. I have four routes around downtown Boulder – 15, 30, 45, and 60 minute walks. All of these walks have the same loop so even when I schedule for a 60 minute walk, I have an easy way to turn it into a 30 minute walk if it’s clear that’s all it’s going to take. Or, if I’m into the first 15 minutes and realize it needs to be an hour, I just extend to the 30 minute segment. My worst case on a walk that goes too long is that I get some steps for my daily Fitbit habit.

Phone calls: I schedule almost all phone calls, except for ones with high priority people. This high priority ones interrupt whatever I’m doing or get done on a drive to and from the office. If you hang around me, you’ll see that my phone rarely rings (except for Amy) and I rarely make calls outbound as most of my world runs on email or real-time messaging.

End everything early: I try to end everything when it’s done. I jump right in and finish when we are finished. When you give things 30 minutes, you don’t have time to futz around with intros and catch ups. When someone starts this way, I break in and say as politely as I can, “What’s on your mind?” On the phone, I minimize chit chat and just try to get to the point. And, after five minutes when we are done, I revel in the notion that I’ve got 25 minutes to do whatever I want.

I’m always experimenting with new things. What do you do to keep meetings manageable and sane?

We Will Never Need Another Financing

I hear some version of this one all the time.

  • “We will never need another financing.”
  • “This financing will get us to cash flow breakeven.”
  • “This is our last financing before we become profitable.”

It’s probably bullshit. There are so many reasons companies raise more money in the future that even making an assertion like this is generally nonsensical. But even if you, as the founder, believe it, you are still probably deluding yourself.

Now, there are points in time where a company doesn’t have to raise any more money. I’m on the board of several significant companies that are profitable and generating meaningful free cash flow. They don’t need to raise any more money unless they want to. And, there are a few reasons they might want to, but we’ll get to that later in the post.

There are also companies, like my first one (Feld Technologies) that bootstrapped and never raised any money. Well – almost no money. We funded the business with $10 (for ten shares of stock) and my dad personally guaranteed a $20,000 line of credit with his bank. We promptly spent the $20,000 on our first few months of operations, realized there was no more where that was coming from, fired everyone, paid back the line of credit over the next six months from our very modest positive cash flow, and then made a profit – and had positive cash flow – every month for the rest of the seven years of the business up until the day we sold the company.

But I’m not talking about bootstrapped companies. I’m taking about angel and VC backed companies. You know, the ones that generally lose money for a while before they make any money. And need money to fund their operations.

Imagine being an investor and being approached by a business SaaS company that has raised $5 million, has $100k / month of revenue, has been growing at about 5% per month, and is doing a $10 million round. “This is the last financing we’ll ever need” is the lead in statement. My first question is “how fast do you want to grow year over year for the next few years?” When the number comes back over 100%, my next question is “Do your customers pay monthly or annually, up front or in arrears.” Unless you are getting paid annually upfront, it’s highly unlikely that your cash coming in is going to outpace your cash going on on a monthly basis for a while. It’s simple math – give it a shot if you want. Sure, every now and then something magical happens (very high price point, very low cost of customer acquisition, zero churn), but that’s a serious edge case.

Now things are working nicely for you and you are growing quickly after raising that $10 million, but you have a competitor that is chasing you from below and a giant public company who is suddenly attacking you from the top. You decide you need to add a direct sales force to augment the self-service / low-touch sales model you’ve been using. Yup – that’ll be more money. Or you realize that you have massive technical debt because you’ve underinvested in scaling and your AWS bills are now increasing non-linearly with your revenue all of a sudden because of the way you’ve architected things. Or you have a major outage and decide you need some redundant infrastructure. I could come up with 100 more items.

You want to do an acquisition, but the seller wants some cash. Your revenue growth flattens out for a few quarters but you didn’t get ahead of the cost dynamic. There is a macro downturn and 25% of your customers vaporize (Don’t think this happens? Ask one of your friends who was a CEO of an Internet company in 2001.)

Where there is a wonderful fantasy about never needing to raise more money, and it does occasionally turn into a reality, I recommend you not lead with it when you are out raising money. It simply undermines your credibility.

In Santa Fe We Wish We Had The Boulder Problems!

There has been a lot of recent noise in Boulder about growth, challenges, and the impact of the tech community on the city. I stirred the pot a little more with my post The Endless Struggle That Boulder Has With Itself. It generated some private emails, including non-constructive troll-like ones such as “Get the fuck out of town, you and people like you are ruining everything” at one end of the extreme to “It’s so frustrating that the all growth is bad crowd is framing the public debate right now and portraying so-called overpaid tech employees as a major cause of all that is wrong in Boulder.”

Andy Alsop, an entrepreneur in Santa Fe who has spent a lot of time in Colorado, sent me a note with some thoughts about his view and experience from working as an entrepreneur in Santa Fe. I asked if he’d write a longer post from his perspective and he took me up on it. Following is a guest post from Andy that I think adds nicely to the discussion.

Don’t get me wrong. I love Santa Fe and I love New Mexico. This is where my kids were born, where three out of the six kids in my family own property and where I have lived for the past 20 years. This is my perspective on why the Boulder City Council should be grateful for the gift it has been given.

I have chosen Colorado as the place where I want to focus the next chapter of my startup life because of its similarities to New Mexico but with the benefit of a rich and diverse tech economy. Since approximately July of 2014 I have been spending half of my time getting to know people in Colorado and half of my time in New Mexico where I work and where my family is currently based. This has allowed me to spend time in Boulder with some exciting startups and some interesting and successful business leaders.

To give you some background, I moved to Santa Fe, NM from the East Coast in 1995 to start a company with my older brother. Prior to making the decision to move out West I asked myself, “Is Santa Fe the right kind of place for me as a technology entrepreneur?” I thought about it for a while before making the move and decided that I was in love with the beautiful outdoors, the endless blue skies, the culture, the great food and the interesting people so with bravado I said to myself “Hell, I’m smart and hardworking and this whole ‘Internet’ thing is everywhere. It doesn’t matter where I live.” As a result, I founded two startups, one of them a spinout from Los Alamos National Laboratory and have been a part of three other startups all of them based on technology.

I find the debate around Boulder’s “dilemma” to be very interesting because Boulder and Santa Fe share a lot of the same characteristics. Both are similar in size, both have educated populations, both are a short drive from a larger city, both are absolutely stunning in terms of the landscape and the outdoors, both are set in the foothills of the Rocky Mountains restricting their ability to grow in all but one direction and both have a high cost of living and a high cost of housing.

In contrast to Boulder, Santa Fe has a stunted economy because it doesn’t share some of the key characteristics of Boulder – including several of the four elements of the “Boulder Thesis” that Brad outlined in his book “Startup Communities.” Santa Fe’s anemic economy is due in large part because Santa Fe has an older population made up primarily of retirees in addition to federal, state and local government workers and service-based workers. We have one “larger” company based in Santa Fe: Thornburg Investment Management which thankfully provides 250 high wage jobs. There are a handful of other smaller companies in Santa Fe but the majority of our businesses are tourism and services based – restaurants, art galleries, hotels, B&B’s, etc. This makes it difficult to make a living in Santa Fe (see Santa Fe’s Living Wage). You will frequently hear people joke about the fact that to make a million dollars in Santa Fe you need to come with two and to live in Santa Fe you must have two to three jobs just to survive. “Young people” come to Santa Fe based on their attraction to the beautiful outdoors and leave when they realize it is difficult to make a living. Santa Fe ends up being a turnstile for young professionals.

Having attempted to recruit experienced knowledge workers to Santa Fe I would always get the same questions from the candidates – “Where are my kids going to go to school?” (While improving, Santa Fe and NM have some of the worst public schools in the country) and “Where am I going to work if your startup doesn’t make it?” Boulder on the other hand has a great school system and a diverse tech economy so that when knowledge workers are recruited to Boulder the recruiter can say “We have great schools and if this position doesn’t work out there are plenty of other places to work.” That means recruits are willing to uproot their families and bring them to Boulder.

So, when I hear members of the Boulder City Council saying “…locals say they don’t like the tech folks…” and the startup economy is attracting “highly paid white men to the city, and they were pricing out families and others” I can’t help but think – Are you crazy? Having a robust tech economy is what many communities like Santa Fe WISH they had. Our civic leaders have to deal with the higher cost of housing from wealthy out of state housing buyers yet the local workers are trying to survive on minimum wage jobs and the government on an insufficient tax base. As a result I have seen NM increasingly tax everything not because it is greedy but because we have to take care of a far poorer population. For instance, the “gross receipts tax” (NM’s version of a sales tax but it is levied on both goods AND services) in Santa Fe has steadily risen from just under 6% 20 years ago to over 8% now and it continues to climb.

Imagine the problems Boulder would have if it were in the same shoes as Santa Fe and didn’t have a thriving tech economy to rely on?  Be Bolder Boulder and embrace the gifts that have been bestowed upon you. Work with the tech community rather than making divisive statements and see the members of your thriving tech economy as your friend and not your enemy.

Interviewing Lucy Sanders at Entrepreneurs Unplugged on 1/28/15

Lucy Sanders, the founder/CEO of the National Center for Women & Information Technology is a remarkable person. I’ve worked with Lucy since 2005 and she’s done more advancing the cause of engaging women in IT, computer science, and entrepreneurship than anyone I know.

As a bonus, she – and NCWIT – are based in Boulder. I like to refer to them as a gem of CU Boulder that is hidden in plain site.

Next Wednesday, as part of the Entrepreneurs Unplugged interview series I’ve been helping host for the past few years, Jill Dupre and I will interview Lucy at the ATLAS Center in Room 100.

I promise you that it will be a special one. Lucy started her career as a young woman at Bell Labs in the 1970s. She was one of the only ones. When she retired from Avaya Labs in 2001, she was CTO, R&D Vice President and Bell Labs Fellow and had about 600 people reporting to her. Her journey up to this point was amazing, but she was just getting started. What she’s done in the last decade as the CEO of NCWIT is amazing.

My work with Lucy has been one of the most satisfying non-profit experiences I’ve been involved in. In addition, I’ve learned an incredible amount from her about the dynamics of women in technology, business, and entrepreneurship. She’s had a dramatic impact on my thinking and behavior and I’d love to share some of her magic with you.

Register here and come join us on Wednesday, January 28, 2015 for 6:00-7:30 PM.

Learning from 2014 Security Hacks

Raj Bhargava (CEO of JumpCloud) and I got into a discussion at dinner the other night about the major security hacks this past year including Sony, eBay, Target, and The Home Depot. Raj spend over a decade in the security software business and it was fascinating to realize that a common thread on virtually all of these major compromises was hacked credentials.

I felt this pain personally yesterday. A bunch of random charges to,, and a few other sites showed up on Amy’s Amex card. We couldn’t figure out where it got stolen from, but clearly it was from another online site somewhere since it’s a card she uses for a lot of online purchases, so I cancelled it. Due to Amex’s endless security process, it took almost 30 minutes to cancel the card, get a new one, and add someone else to the account so I wouldn’t have to go through the nonsense the next time.

In my conversation with Raj, we moved from basic credential security to the notion that the number of sites we access is exploding. Think about how many different logins you have to deal with each day. I’m pretty organized about how I do it and it’s still totally fucked.

Every major new service is managed separately. Accounts to AWS or Google Compute Engine or Office 365 are managed separately. Github is managed separately. Google Apps are managed separately. Every SaaS app is managed separately. All your iOS logins are yet another thing to deal with. The only thing that isn’t managed separately are individual devices – as long as you have an IT department to manage them. Oh wait, are they managing your Mac? How about your iPhone and other BYOD devices? Logins and passwords everywhere.

Raj’s assertion to me at our dinner was that there are too many different places, and too many scenarios, where something can be compromised. For instance, some companies use password managers and some don’t. Some companies that take password management to an individual level – where a single employee manages her own passwords – end up with many login / password combinations which are used over and over again. Or worse, the login / password list ends up in an unencrypted file on someone’s device (ahem Sony.)

If you are nodding, you are being realistic. If you aren’t nodding, do a reality check to see if you are in denial about your own behavior or your organization’s behavior. Think about how new services enter your organization. A developer, IT admin, marketing person, executive, or salesperson just signs up for a new online service to try. When doing so, which credentials do they use? If it is connecting to your company’s environment, it’s likely they are using your organization’s email address and a verbatim password they use internally as well. That’s a recipe for getting hacked.

So, Raj and I started discussing solutions. Some of it may just be unsolvable as human nature may not let us completely protect users online. But it seems like there are areas where we can make some immediate headway.

  • Secure directory services (the approach JumpCloud is taking)
  • Multi-factor authentication has become all the rage (I use it)
  • Different strong passwords for each service, possibly via a password manager like LastPass (which is what I use)

What other approaches exist that would scale up from small (10 person orgs) to large (100,000 person orgs) and provide the same level of identity and credential security?