The Gift of Insight

Jonathan Schwartz has a great post entitled “Every Customer Visit is a Lesson.” It’s so true…if you want to give yourself a gift this holiday season, give yourself the gift of insight and spend some time in the market with a few of your top customers or prospects.  I’ve always found that to be one of the most valuable ways to shape the business, both strategically and operationally.

One of the most vivid memories I have to illustrate this concept is a meeting that I had with Crate and Barrel, a prospect, in the very early days of Return Path, back in 2000 or 2001.  I went in with my colleague Sophie Miller, and with a number of product sales specialists from our reseller, DoubleClick, for an all-day session with C&B’s online marketing team.  We collectively were pitching everything, possibly including the kitchen sink — ad serving through DART, buying online media through the DoubleClick Network, using Abacus to expand the reach of their catalog, sending email through DARTMail, renting email lists through DoubleClick’s email list business, oh yes, and using Return Path’s ECOA service to keep their email database clean.

The meeting was a mess, and as far as I can tell, it didn’t really lead to any meaningful business, either for us or for DoubleClick.  I learned two things in this call the hard way, but both were incredibly valuable lessons that continue to shape our business today.

First, we created massive confusion by bringing multiple sales people in to each present a specific product to the customer, rather than sending in one senior, consultative sales person to present a holistic digital marketing solution.  Picture yourself as the head of e-commerce for a major retailer, expecting an insightful day with the leading vendor in the space…then walking into the meeting and seeing that vendor’s SEVEN different sales people introducing themselves to each other!  It was a mess.  Since then, we have tried hard (and I think DoubleClick has as well) to run with a single sales force organized around the customer, not organized around our own products.

Second, we discovered that the original version of our flagship ECOA product (which was still in beta at the time) had a couple of flaws in the business model that were probably going to make it a non-starter in the retail/catalog vertical.  We also learned, happily, that the client loved the concept, but there were some details in the original product that had to be fixed if we were ever going to get traction with key customers in that key segment.  We fixed these problems and were able to successfully re-launch ECOA later that year, but more important, we now stay much closer to our customers as we develop new products and features so we make sure concepts are more firmly market tested before they head into development.

There are many more examples of this Gift of Insight, which I’ll share in future posts.  Happy Holidays!

Right, That’s MY Job

I made a dumb comment at our recent Board meeting that got me thinking.  We came into the meeting with, in addition to lots of the regular updating and reporting, one specific strategic topic we wanted guidance on from the Board about something that’s been nagging the management team for a while without an obvious solution.

We had a great conversation about the topic with the Board and got very clear guidance as to their perspective on what we should do.  I agreed with most of it, albeit with a couple modifications, but more than anything else, I was happy for the note of clarity on an issue with which we’d been struggling as a management team. 

So my comment in the meeting was "that’s pretty clear direction, we’ll go do that" (or something along those lines).  Whereupon one of my Board members politely reminded me that actually it’s not the Board’s job to make things happen, only to give advice and counsel, and that I shouldn’t take their words as gospel and assume they’ll work.  Right.  Good point.

The Board is my boss (I am on the Board, but so are five other people), and while there are some items where the Board does have the final say, the overwhelming majority of my actions and the actions within the company are really up to us.  We can seek guidance when we feel we need it, but that guidance doesn’t come with a guarantee that it will work operationally — nor does it give me the ability to absolve myself if things don’t work out in the end.

This is a point worth thinking about no matter what role you play in your organization.  Most people, most of the time, have a lot of latitude in how they go about their job.  Sometimes, the boss tells you what to do.  But most of the time, you’re on your own, and while you can and should get advice from above when necessary, the most successful people in business are the ones that take the guidance and factor it into their own decision-making and initiative as opposed to blindly following.

It’s fairly rare in a startup or scaleup that you, as a CEO or CXO (Chief [fill in the function] Officer) of any kind, will have significant one-on-one time with other members of the executive suite; instead, you’re most likely to spend time with the team in executive meetings, at offsites, or during all-company events. So, when you do get that one-on-one time it’s important to make sure that it’s not only productive, but that it builds a stronger relationship between you and the other person.

As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of work and non-work settings.  By that I mean, working together on some aspect of their part of the business. Since each role and each person performing that role are different, there aren’t any hard and fast rules, but I thought I would create a series of posts that provide some ideas on things I’ve done to develop a better relationship, better team, and better company for each CXO in a company. 

I also have a whole series of posts related to each function on the executive team — CFO, CMO, CTO, etc.  So each post is part of two series.  This is the inaugural for both, and it’s quite fitting as Q4 is, for most companies, budgeting and planning season.  So today’s topic is How I engage with the CFO.

When I get the chance to spend time with my CFO I’ve found that we both get the most value working on several “problems” together. For example, we do Mental Math together where we look at key metrics and test them, improve them, or decide to scrap them. We are always attuned to key metrics and from time to time, we project them forward in our minds. What will happen to a key metric if our business scales 10-fold or if it declines 10-fold, for example. 

We are constantly checking to see that our financial and operating results mesh with our mental math.  When looking at our cash balance, we’ll look back at the last financial statement’s cash number and mentally work our way to the current statement: operating profits or losses, big swings in AR or AP, CapEx, and other “below the line” items. Do they add up?  Can we explain what we’re seeing in plain English to other leaders or directors?  The same thing applies to operating metrics — the size of our database, our headcount, our sales commission rate, and so on.

I’ve found that by working on the mental math that we actually come to understand the dynamics of the business far better than merely looking at the numbers or comparing the numbers. The mental math approach forces both you and the CFO to engage with the results, question them, and anticipate how slight changes can impact the company going forward. And once you get to that point, you have the ability to creatively think about how you want to go forward.  Here’s a simple example from the early days of Return Path.  One day, my long-time business partner and CFO Jack and I were doing mental math around how many clients each of our Customer Success team members was handling.  We had an instinct that it wasn’t enough — and we did a quick “how many of those reps would we need if we were doing $100mm in revenue” check and blanched at the number we came up with.  That led to a major series of investments in automation and support systems for our CS team.

Another way that the CFO and I work together is in a game called “spotting the number that seems off.” In any spreadsheet or financial analysis there is bound to be something that doesn’t seem quite right and for some uncanny reason, I am really good at finding the off number. I’m sure this has driven CFOs crazy over my career, but for whatever reason I have some kind of weird knack for looking at a wall of numbers and finding the one that’s wrong.  It’s some combination of instincts about the business, math skills, and looking at numbers with fresh eyes. It’s not an indictment on the CFO’s results and it’s not a “gotcha” moment but it’s part of the partnership I have with my CFO that improves the quality of our work and quantitative reasoning. My hunch is that looking at something with fresh eyes, as opposed to being the person who produces the numbers in the first place, makes it easier to spot something that’s not quite right. Kind of like an editor working with you on an article or book—they always seem to pick up and point out something that you didn’t see even though you spent hours creating it and hours more reading and re-reading something.

A third way to work with the CFO is to create stories with numbers. The best CFOs are the ones who are also good communicators — but that only partly means they are good at public speaking.  Being able to tell a story with numbers and visuals is an incredibly important skill that not all CFOs possess.  Whether the communication piece is an email to leaders, a slide at an all-hands meeting, or a Board call, partnering with a CFO on identifying the top three points to be made and coming up with the relevant set of data to back the number up — and then making sure the visual display of that information is also easy to read and intellectually honest, can be the difference between helping others make good decisions or bad ones.

Of course, a CFO could create stories on their own but like much of storytelling (like screenwriters for movies, plays, or sitcoms, for example), the creative storytelling usually happens with a team. In presenting financial data to others so that it makes an impact, so that it motivates them to take an action or change a behavior, a team approach is best and the CEO-CFO team can be much more effective than either one of them alone.

You won’t have a lot of time to spend 1:1 with any given CXO on your team, including the CFO, but you can make the time you spend together work to your favor in developing a stronger relationship between you and the CFO, and help you build a stronger company that can scale quickly. Without a deep understanding and strong relationship with others on your leadership team, your decision-making, speed, and risk-taking can suffer. Make sure every minute you spend with the CFO is productive. That’s why working on things together like mental math, spotting the off number, and storytelling, can be powerful ways to help you build a better company. 

(Also posted to the Bolster Blog).

The Best Place to Work, Part 7: Create a Thankful Atmosphere

My final installment of this long series on Creating the best place to work (no hierarchy intended by the order) is about Creating a thankful atmosphere.

What does creating a thankful atmosphere get you?  It gets you great work, in the form of people doing their all to get the job done.  We humans – all of us, absolutely including CEOs – appreciate being recognized when they do good work.  Honestly, I love what I do and would do it without any feedback, but nothing resonates with me more than a moment of thanks from someone on my exec team or my Board.  Why should anyone else in the organization be any different?

This is not about giving everyone a nod in all-hands by doing shout-outs.  That’s not sustainable as the company grows.  And not everyone does great work every week or month!  And it’s not about remembering to thank people in staff meetings, either, although that’s never bad and easier to contain and equalize.

It is about informal, regular pats on the back.  To some extent inspired by the great Ken Blanchard book Whale Done, and as I’ve written about before here, it’s about enabling the organization to be thankful, and optimizing your own thankfulness.

Years ago we created a peer award system on our company Intranet/Wiki at Return Path.  We enable Peer Recognition through this.  As of late, with about 350 employees, we probably have 30-40 of these every week.  They typically carry a $25 gift card award, although most employees tell me that they don’t care about the gift card as much as the public recognition.  Anyone can nominate anyone for one of the following awards, which are unique to us and relevant to our culture:

• EE (Everyday Excellence) -is designed for us to recognize those who demonstrate excellence and pride in their daily work.
• ABCD (Above and Beyond the Call of Duty) -is designed for us to recognize the outstanding work of our colleagues who go Above and Beyond their duties and exemplify exactly what Return Path is about
• WOOT (Working Out Of Title) -is designed for us to recognize those who offer assistance that is not part of their job responsibilities.
• OTB (On The Business)-is about pulling ourselves out of day-to-day tasks and ensuring we are continually aligned with the long-term, strategic direction of the business.  We make sure we’re not just optimizing our current tasks and processes but that we’re also thinking about whether or not we should even be doing those things.  We stop to think outside of the “box” and about the interrelationship between what we are doing and everything else in the organization.  In doing so, we connect the leaves, the branches, the trunk, the roots and soil of the tree to the hundreds of other trees in the forest.  We step back to look at the big picture
• TLAO ( Think Like An Owner)-means that every one of us holds a piece of the Company’s future and is empowered to use good judgment and act on behalf of Return Path.  In our day-to-day jobs we take personal responsibility for our products, services and interactions.  We spend like it’s our own money and we think ahead.  We are trusted to handle situations like we own the business because we are smart people who do the right thing.  We notice the things happening around us that aren’t in our day-to-day and take action as needed even if we’re not directly responsible
• Blue Light Special  is designed for us to recognize anyone who comes up with a clever way to save the company money)
• Coy Joy Award is in memory of Jen Coy who was positive, optimistic and able to persevere through the most difficult of circumstances.  This award is designed to recognize individuals who exemplify the RP values and spread joy through the workplace.  This can be by going above and beyond to welcome new employees, by showing a high degree of care and consideration for another person at RP, by being a positive and uplifting influence, and/or making another person laugh-out-loud.
• Human Firewall is awarded if you catch a colleague taking extra care around security or privacy in some way, maybe a suggestion in a meeting, a feature in a product, a suggestion around policy or practice in the office.

In the early days, we read these out each week at All-Hands meetings.  Today at our scale, we announce these awards each week on the Wiki and via email.  And I and other leaders of the business regularly read the awards list to see who is doing what good work and needs to be separately thanked on top of the peer award.

Beyond institutionalizing thanks…in terms of you as an individual person, there are lots of ways to give thanks that are meaningful.  Some are about maximizing Moments of Truth.  Another thing I do from time to time is write handwritten thank you notes to people and mail them to their homes, not to work.  But there are lots of ways to spend the time and mental energy to appreciate individuals in your company in ways that are genuine and will be noticed and appreciated.  To some extent, this paragraph (maybe this whole post) could be labeled “It’s the little things.”

That’s it for this series…again, the final roundup for the full series of Creating the Best Place to Work is here and individual posts are here:

1. Surround yourself with the best and brightest
2. Create an environment of trust
3. Manage yourself very, very well
4. Be the consummate host
5. Be the ultimate enabler
6. Let people be people
7. Create a thankful atmosphere

Anyone have any other techniques I should write about for Creating the Best Place to Work?

Sophisticated Negotiation Technique

Brad and our co-tenants in Colorado, Still Secure, have already documented this — including a dedication from Still Secure (thanks, guys – you took the words right out of my mouth).  But still, the story must be recorded here for posterity as well, if for no other reason than how absurd it was.

We share a lease in Colorado with Still Secure (the lease used to be Brad’s/Mobius’s), and the lease ends this fall.  Both we and Still Secure have grown to the point where we’re bursting at the seams, so someone is going to have to move out.  After months of polite wrangling, it was clear there was no easy solution.  Sometimes, win-win just doesn’t exist.

So we did what any civilized bunch of people would do.  We flipped a coin.  It just seemed more entertaining in the end than rock-paper-scissors.  And unfortunately, we came up short.  But we had pre-negotiated a buy-out with Still Secure whereby the party who got to keep the space paid $X to the other party to cover moving expenses, furniture, and presumably pain and suffering, so now we have a full piggy bank to go procure and set up new space for ourselves.

Harvard Program on Negotiation — do I see a case study in the works?

Lean In, Part II

My post about Sheryl Sandberg’s Lean In a couple months ago created some great dialog internally at Return Path.  It also yielded a personal email from Sheryl the day after it went up encouraging me to continue “talking about it,” as the book says, especially as a male leader.  Along those lines, since I wrote that initial post, we’ve had a few things happen here that are relevant to comment on, so here goes.

We partnered  with the National Center for Women & IT to provide training to our entire organization on unconscious bias.  We had almost 90% of the organization attend an interactive 90 minute training session to explore how these biases work and how to discuss these issues with others.   The goals were to identify what unconscious bias is and how it affects the workplace, identify ways to address these barriers and foster innovation, and provide practice tools for reducing unconscious biases.   While the topic of unconscious bias in the workplace isn’t only about gender, that’s one major vector of discussion.  We had great feedback from across the organization that people value this type of dialog and training.  It’s now going to be incorporated into our onboarding program for new employees.

Second, as I committed to in my original post, we ran a thorough gender-based comp study.  As I suspected, we don’t have a real issue with men being paid more than women for doing the same job, or with men and women being promoted at different rates.    That’s the good news.  However, the study and the conversations that we had around it yielded two other interesting conclusions.  One is that that we have fewer women in senior positions than men, though not too far off our overall male:female ratio of 60:40.  On our Board, we have no women.  On our Executive Committee, we have 1 of 10 (more on this below).  On our Operating Committee, we have 8 of 25.  Of all Managers at the company, we have 32 of 88.  So women skew to more junior roles.

The other is that while we do a good job on compensation equity for the same position, it takes a lot of deliberate back and forth to get to that place.  In other words, if all we did was rely on people’s starting salaries, their performance review data, and our standard raise percentages, we would have some level of gender-based inequality.  Digging deeper into this, it’s all about the starting point.  Since we have far more junior/entry level women than men, the compensation curve for women ends up needing to be steeper than that of men in order to level things out.  So we get to the right place, but it takes work and unconventional thinking.

Finally, I had an enlightening process of recruiting two new senior executives to join the business in the past couple of months.   I knew I wanted to try and diversify my executive team, which was 25% female, so I made a deliberate effort to focus on hiring senior women into both positions.  I intended to hire the best candidate, and knew I’d only see male candidates unless I intentionally sourced female candidates.  For both positions, sourcing with an emphasis on women was VERY DIFFICULT, as the candidate pools are very lopsided in favor of men for all the reasons Sheryl noted in her book.  But in both cases, great female candidates made it through as finalists, and the first candidate to whom I offered each job was female – both superbly qualified.  In both cases, for different reasons I can’t go into here, the candidates didn’t end up making it across the finish line.  And then in both cases, when we opened up the search for a second round, the rest of the candidate pool was male, and I ended up hiring men into both roles.  Now my resulting exec team is even more heavily male, which was the opposite of my intention.  It’s very frustrating, and it leaves us with more work to do on the women-in-leadership topic, for sure.

So…some positives and some challenges the last few months on this topic at Return Path.  I’ll post more as relevant things develop or occur.  We are going to be doing some real thinking, and probably some program development, around this important topic.

It feels as if almost everyone in our industry has read the famous Netflix culture deck on Slideshare, and with over 5mm views, that may not be too far off.  If you haven’t looked at it before, and if you care about your organization’s culture and how productive and happy employees are the best kind of employees, then take the time to flip through it.

As part of a benchmarking exercise we did on employers with unique and best HR/People practices a few years ago, a few of us did either site visits or at least live interviews with leaders at four companies, all of whom are pretty well known for progressive People practices that are also in-line with our company’s culture:  Morningstar, Gore, Nucor, and Netflix.  As part of this, we met in person with Patty McCord, Netflix’s long-time head of People.  It was a really informative meeting.

Now Patty has written a longform article in Harvard Business Review that shares a lot of what we learned from her in her office that day. It’s absolutely worth a read.  Netflix does have a pretty distinct culture and gets positive but mixed reviews on Glassdoor, so as with everything, I’m not advocating adopting everything they do lock, stock, and barrel.  But I can guarantee that some of the lessons that Patty shares are valuable no matter what your company is like.

(Written by both my Bolster co-founder Cathy Hawley and me)

I’ve attended two remote conferences, which Cathy dubbed “Zoomsites” — one here at Bolster and the Foundry Group CEO Summit.  Both hold interesting lessons for how these kinds of events can work well.

We founded Bolster two months into the COVID-19 pandemic, and our founding team had not met in person after 6 months of working together. Now, luckily, we’ve all worked together for many years, so we have a lot of trust built up, and have a very strong operating system which includes full team daily standups. Still, nothing beats face-to-face interaction. If you’ve ever founded a startup, you know how impactful it can be to work side by side, bounce ideas off each other, and collaborate as you learn more about opportunities and challenges in your market. 

We also have a strong belief in the power of the team, and the need to work together to ensure that we are aligned on all aspects of the business. And, we had a successful launch, with more interest in our marketplace than we had anticipated, so we knew we needed to step back to have a planning and strategy session.

We’ve done many executive offsites, and couldn’t imagine having an impactful offsite remotely, and we all agreed that we would be comfortable meeting up in person. So we started planning a 2-day offsite together in New York. Unfortunately, it turned out visitors to NY from Colorado and Indiana, the two states we were traveling from, needed to quarantine for 10 days when they got to NY. While technically we could get around this because we weren’t staying for 10 days, we decided to follow the spirit of the rules, and cancel our travel.

Since we really needed to have the planning and strategy session, and we’d blocked the two full days on our calendars, we decided to test out a ‘zoomsite’ – an all-remote video call. We modified the agenda a little – some things good in person fall flat on video. We knew we wanted to have really engaging conversations, and keep the agenda moving along, so that all eight of us could fully participate and complete the necessary work. I’m happy to say that we came out of the offsite with a revised strategic plan, new six-month goals set, and owners for each of the different workstreams. And, we had fun. Success!

The Foundry Group CEO Summit has been a different animal — it’s wrapping up today, but there’s been enough of it so far this week to comment on.  Foundry took a regular annual event with a large group (50-75) and moved it online.  They did a great job of adapting to the medium, spreading the event out with a few hours a day over multiple days to avoid Zoom fatigue and optimize attendance; scheduling content in shorter bursts than usual; making good use of breakout room technology; and encouraging heavy use of Zoom’s chat feature during sessions to make it as interactive as possible.  Like the Bolster event, there were some elements missing — all the great “hallway conversations” you have at in-person conferences where people are staying in the same hotel and seeing each other at meals, in the gym, between sessions, etc.  But it has also been a big success with enough community elements to make it worthwhile. 

Want to have a Zoomsite? Here are some tips:

• Make sure you have the tools needed for each activity. When you are brainstorming in person, you may use sticky notes or flip charts to write on. Remotely, you can use Google Docs or Sheets or tools like Note.ly or Miro
• Prep the sheets or docs ahead of time, so that people can engage in the activities easily. At our Zoomsite, we modified our blue-sky brainstorm session so that we each answered a few questions in a Google Sheet. We had a separate section for each person, and the exercise was easy to understand and engage in, and people got straight to work.
• Schedule in more breaks, shorter sessions, or less than full-day meetings. We had a couple of hour-long breaks during the day, which helped people to focus.  Foundry did a great job of getting everyone’s attention for a few hours every day, for more days than a normal in-person conference
• Plan your technology. At the Bolster meeting, we learned this the hard way. We tested out the idea of doing a “walk and talk” session where we’d each walk in our neighborhoods, and have a couple of strategic conversations just on the phone. Unfortunately, the technology didn’t work for everyone, as they hadn’t all used Zoom on their phones before, it was windy in some locations, and cell service dropped people from time to time.  Probably not the best idea we had!
• Include a social component. We were a little skeptical about this at the Bolster Zoomsite, but we’d always incorporated social time into offsites, and we really value connecting as people, not just as professionals, so we gave it a try. On the second day of our Zoomsite, we took a 2 hour break at the end of the day, and came back for drinks and dinner together. We had personal conversations, including sharing our favorite tv shows. Eight people on video eating together might sound odd, and we weren’t sure if it would work, but we all agreed that it was fun, and we’d do it again.  I missed the Foundry “Virtual Fun” session, but they did a virtual game show run by our sister portfolio company, Two-Bit Circus (and also had investigated Jack Box Games as another option for virtual games via Zoom screen share plus real-time voting and other engagement via phone).  I heard that session was great and engaging from people who attended

We all hope life returns to some kind of normal in 2021, though it’s unclear when that will be.  And there’s definitely value to doing meetings like this in person, but at least we now know that we can have a successful remote offsite or larger conference event.  As with everything, it will be interesting to see how the world is changed by COVID.  Maybe events like this will figure out how to mix remote and in-person participation, or alternate between event formats to keep travel costs down.

In addition to our work on helping CEOs understand board-building best practices, which I posted about last week, I’ve spent the past several months publishing a second series of blog posts to help current and aspiring directors (really, any senior executive!) understand the behind-the-scenes details of private company board service. This second series is also now an eBook and its content will also feature in the upcoming second edition of Startup Boards that I’m collaborating on with Brad Feld and Mahendra Ramsinghani.

When Bolster published the findings of our Board Benchmarking study, we revealed that 4 out of 5 seats on private company boards today are held by individuals who are white, and 86% of director seats are held by men.

And we also learned that 2 out of 3 CEOs are open to bringing on first-time directors to their boards, largely to help add some much-needed diversity to the most senior ranks of corporate service. To assist current and aspiring board directors out there, we decided to aggregate our team’s collective brainpower to shed light on how to get recruited for a board role, what to expect once you’re there, and how to make an impact.

You can see the full list of blog posts here:

• Introduction to Startup Boards
• How to Prepare Yourself to Get on Your First Board
• Should You Serve on an Advisory Board?
• Interviewing for a Board Role
• What You Need to Know About Board Compensation
• Preparing for Your First Board Meeting
• Corporate Governance as a Board Member
• How to Be a Great Board Member
• When Things Aren’t Black and White: How to Deal with Murky Areas
• Giving Difficult Feedback and Making Your Voice Heard
• How to Know if You’re Doing a Good Job as a Board Member

You can download all of these in an eBook, How to Succeed in Your First Board Role, from the Bolster web site.

We hope this book helps inspire and empower you on your own journey as a board director. And if you’d like to get access to more exclusive content like this and be considered for a board role in the future, you can sign up as a Bolster member here.

Techstars Roundup:  Why I Mentor Other Entrepreneurs

Yesterday was Demo/Investor day at Techstars in Boulder, Colorado.  A lot of people have written about it – Fred, Brad, and a great piece by Don Dodge on TechCrunch listing out all the companies.  My colleague George and I co-mentored two of the companies, SendGrid and Mailana, and we really enjoyed working with Isaac and Pete, the two entrepreneurs.

I posted twice earlier this summer on the TechStars experience.  My first post on this, Where do you Start?, was about whether to be methodical in business planning for a startup or dive right into the details.  My second post, One Pitfall to Avoid, was about making sure you don’t create a whizzy solution looking for a problem, but that you start with a problem that needs solving.

Rather than rehash what others have written about yesterday — yes, it was great and fun and energizing — I thought I’d focus on why I spend time mentoring new entrepreneurs.  I did it this year at TechStars, but I’ve done this informally for probably a dozen different entrepreneurs over the years in the community in general. 

Anyway, there are four main reasons I spend time mentoring other entrepreneurs (in no particular order):

It sharpens the saw.  This is Stephen Covey’s language from both The 7 Habits of Highly Effective People and The 8th Habit:  From Effectiveness to Greatness, and it simply refers to an activity that puls you out of the day to day and refreshes your brain because it’s different.  Running, playing guitar, mentoring sessions with entrepreneurs — they all clear the head and are just plain fun.

I get good specific ideas for my own business.  I think I came away from every single meeting I had with either entrepreneur this year with at least one new “to do” for myself and my team at Return Path.  There’s nothing quite like seeing how another company or entrepreneur operates to spur on good thinking, and in this case, both teams we worked with were working in the email space, so they were very relevant to our day-to-day.

I crystallize my own thoughts and ideas.  Much like writing this blog, problem/solution sessions with other entrepreneurs forces me to take a cloud of ideas down to a simple sentence or paragraph. 

I learn a lot about my colleagues.  This is a specific case for this year because I co-mentored these companies with George, although I guess bits and pieces of it have come up over the years as I’ve roped other colleauges into other situations.  George and I brought different ideas and frames of reference to our sessions with SendGrid and Mailana, and it was fun for me and a good learning experience as well to see how George approached the same problems I did.  Call it a “peek inside George’s brain.”

Hopefully I will get invited back to TechStars again next year as a mentor – it was great fun, and I’m incredibly proud of Pete and Isaac and their teams with how well they presented their companies yesterday!

Everything That is New is Old

With a full nod to my colleague Jack Sinclair for the title and concept here…we were having a little debate over email this morning about the value of web applications vs. Microsoft (perhaps inspired by Fred, Brad, and Andy’s comments lately around Microsoft vs. Apple).

Jack and his inner-CFO is looking for a less expensive way of running the business than having to buy full packages of Office for every employee to have many of them use 3% of the functionality.  He is also even more of a geek than I am.

I am concerned about being able to work effectively offline, which is something I do a lot.  So I worry about web applications as the basis for everything we do here.  We just launched a new internal web app last week for our 360 review process, and while it’s great, I couldn’t work on it on a plane recently as I’d wanted to.

Anyway, the net of the debate is that Jack pointed me to Google Gears, in beta for only a month now, as a way of enabling offline work on web applications.  It clearly has a way to go, and it’s unclear to me from a quick scan of what’s up on the web site whether or not the web app has to enable Gears or it’s purely user-driven, but in any case, it’s a great and very needed piece of functionality as we move towards a web-centric world.

But it reminded of me of an application that I used probably 10-12 years ago called WebWhacker (which still exists, now part of Blue Squirrel) that enables offline reading of static web pages and even knows how to go to different layers of depth in terms of following links.  I used to use it to download content sites before going on a plane.  And while I’m sure Google Gears will get it 1000x better and make it free and integrated, there’s our theme — Everything That is New is Old.

The iPhone?  Look at Fred’s picture of his decade old Newton (and marvel at how big it is).

Facebook?  Anyone remember TheSquare.com?

MySpace?  Geocities/Tripod.

LinkedIn?  GoodContacts.

Salesforce.com?  Siebel meets Goldmine/Act.

Google Spreadsheets?  Where to begin…Excel…Lotus 123…Quattro Pro…Visicalc/Supercalc.

RSS feeds?  Pointcast was the push precursor.

Or as Brad frequently says, derive your online business model (or at least explain it to investors) as the analog analog.  How does what you are trying to online compare to a similar process or problem/solution pair in the offline world?

There are, of course, lots of bold, new business ideas out there.  But many successful products in life aren’t version 1 or even version 3 — they’re a new and better adaptation of something that some other visionary has tried and failed at for whatever reason years before (technology not ready, market not ready, etc.).