Dumb Money

I don’t have a counter cliche to Fred’s two-for-one this week on Passing the Hat and Ponying Up, but I’ll counter with a different, somewhat related Fred cliche that I was reminded of today when reading Paul Graham’s essay entitled A Unified Theory of VC Suckage (form your own opinions of it, but it’s nothing if not thorough and experience-based).

There’s nothing worse than dumb money backing a dumb idea or management team.

The dumb idea or team can destroy an emerging sector pretty quickly, and the dumb VC behind the deal will just keep ponying up.  For the record, the converse is also true — there’s nothing better than smart money behind a great idea and solid team.

The classic dot com version of dumb money is the company who decides to give away its core service for free (the one where they compete with other players) in order to try to make money at something else.  It could take 2 years and a ton of VC money before that company is out of business, having figured out that they needed to charge for their core business — and that process can wash out other companies in the process who are being smarter and more conservative about things.

So instead of just cheering that your competitor is dumb, dig in and look at how smart the money is behind the company.  If the money is dumb, too, beware!

Ratcheting Up Is Hard To Do (or Boiling the Frog, Part II)

I’ve had to ratchet down business several times over the years at Return Path.  Times were tough, revenues weren’t coming as fast as promised, my investors and I were growing weary, the dot com crash, etc. etc.  We had layoffs, consolidated jobs, cut salaries multiple times, made people wear 8 hats to get the job done.  It’s an awful process to go through.

In the last year or so, business has finally started going much better.  We’ve been fortunate in many ways that we’re still around, with products that work really well, with a good customer base, and with good and patient investors and employees, as the business climate has improved.  We’ve grown from 22 people (at our low point) up to almost 75.  But what that has meant for our organization is that we’ve had to quickly "ratchet back up," adding people, adding new functions that were previously one of many hats worn by a single person, operating at a different level.  While ratcheting down is a nightmare, it turns out that quickly ratcheting back up is in many ways just as hard on the organization.

Some examples:

– IT (internal email and servers) has been run by a part-time resource and "off the side of the desk" of our product development engineering department.  Now it is almost completely broken, and it turned out we hired a very talented IT manager, probably about three months too late.

– Staffing up is particularly tough without a dedicated HR function and with a legacy of missed budgets.  HR has been done off the side of the desk of me and my executive assistant, and we can’t keep pace any more with all the recruiting, hiring, training, and development planning.  Now that we feel like we need and can afford more staff, we need to hire an HR manager to handle it all, but we need someone in place and trained today, not three months from now.

– A 22 person company can function brilliantly as a network of Individual Contributors who loosely coordinate with each other.  But now what we need at 75 is a a few hardcore Managers that can build systems and processes so that the whole machine runs smoothly.  We don’t necessarily have those people in-house, and if we bring them in from the outside, I’m left wondering if the Individual Contributors will feel like their years of hard work aren’t appreciated if there’s a new layer of management surrounding them.

I hope we never have to ratchet down again…but part of the reason why now is that I never want to have to ratchet back up, either!

Thanks to my COO and business partner Jack Sinclair for his help with this posting.

Email Marketing 101

We just published a book!  Sign me Up! A marketer’s guide to creating email newsletters that build relationships and boost sales is now available on Amazon.com.  The book is authored by me and my Return Path colleagues Mike Mayor, Tami Forman, and Stephanie Miller.  What’s it about?

– At its core, the book is a very practical how-to guide.  Any company — large or small — can have a great email newsletter program.  They’re easy, they’re cheap, and when done well, they’re incredibly effective.

– This book helps you navigate the basics of how to get there, covering everything from building a great list, to content and design, to making sure the emails reach your customers’ inboxes and don’t get blocked or filtered.

– Our central philosophy about email marketing, which permeates the advice in the book, is covered in my earlier New Media Deal posting (which is reproduced in part in the book’s Preface) — that customers will sign up for your email marketing in droves if you provide them a proper value exchange for the ability to mail them.

– I’d encourage you to buy the book anyway, but in case you need an extra incentive, we are also donating 10% of book sales to Accelerated Cure, a research organization dedicated to finding a cure for Multiple Sclerosis, in honor of our friend and colleague Sophie Miller.

More postings to come about the process of writing, publishing, and marketing a book in 2005 — boy was the experience we had different than it would have been 10 years ago.

Americans have long operated under an unwritten deal with media companies (for our purposes here, let’s call this the Old Media Deal). The Old Media Deal is simple: we hate advertising, but we are willing to put up with an amazing amount of it in exchange for free or cheap content, and occasionally one of those ads slips through to the recesses of our brain and influences us in some way that old school marketers who trade in non-addressable media can only dream of. Think about it:

– 30 minutes of Friends has 8 minutes of commercials (10 in syndication!)
– The New York Times devotes almost 75% of its total column inches to ads
– We get 6 songs in a row on the radio, then 5 minutes of commercials
– The copy of Vogue‘s fall fashion issue on my mom’s coffee table is about 90% full page ads

The bottom line is, advertising doesn’t bug us if it’s not too intrusive and if there’s something in it for us as consumers.

Since I started working in “New Media” in 1994, I’ve thought we had a significantly different New Media Deal in the works. The New Media deal is that we as American consumers are willing to share a certain amount of personal information in exchange for even better content, more personalized services, or even more targeted marketing — again, as long as those things aren’t too intrusive and provide adequate value. Think about how the New Media Deal works:

– We tell Yahoo that we like the Yankees and that we own MSFT stock in order to get a personalized home page
– We tell Drugstore.com what personal health products we buy so we can buy our Q-tips and Benadryl more quickly
– We tell The New York Times on the Web our annual income in order to get the entire newspaper online for free
– We let PayTrust know how much money we spend each month so that we can pay our bills more efficiently
– We let Google scan our emails to put ads in in them based on the content to get a free email account
– We give their email address out to receive marketing offers (even in this day and age of spam) by the millions every day

Anyway, after a few years of talking somewhat circuitously about this New Media Deal, my colleague Tami Forman showed me some research the other day that backs up my theory, so I thought it was time to share. In a study conducted by ChoiceStream in May 2004, 81% of Internet users expressed a desire for personalized content; 64% said they’d provide insight into their preferences in exchange for personalized product and content recommendations; 56 would provide demographic data for the same; and 40% said they’d even agree to more comprehensive clickstream and transaction monitoring for the same. All of these responses were stronger among younger users but healthy among all users. Sounds like a New Media Deal to me.

Don’t get me wrong — I still think there’s a time and a place for anonymity. It’s one of the great things about RSS for certain applications. And privacy advocates are always right to be vigilant about potential and actual abuses of data collection. But I think it’s becoming increasingly clear that we have a New Media Deal, which is that people are willing to sacrifice their anonymity in a heartbeat if the value exchange is there.

P.S. Quite frankly, I wish I could give spammers a little more personalized information sometime. They’re going to email me anyway — they may as well at least tell me to enlarge a part of my body that I actually have.

Mail Fusion

For 8 or 9 years now, we haven’t received a single bill by U.S. mail.  We use PayTrust (originally PayMyBills.com) for “online” bill pay.  We have a P.O. Box somewhere in South Dakota that we’ve redirected all our bills to.  The bills get opened, scanned, we get an email, we enter in a payment amount and date.  No fuss, no muss.  PayTrust even figures out which bills can be electronically delivered and provides an easy interface to set that up directly into the PayTrust account as well.  I haven’t received a bill or written a check in years.  I think we pay something like $9/month for the service.

I just ran across a new service this week called Earth Class Mail (thanks to my colleague Alex Rubin for pointing this out) that does the same thing for ALL of your snail mail, with a twist.  You direct all your mail (presumably not magazines) to a P.O. Box, and they first scan in all the envelopes.  You see them and decide what to do with each item — forward to you, scan in and show you online or via pdf, recycle, shred, etc.  The cost seems to range from $10-60/month depending on volume.

Certainly a good idea, at least for people who travel a lot or people who have to pay for a P.O. Box anyway (not sure it’s for everyone), and another interesting service where email takes center stage as the mission critical delivery vehicle.

The Good, The Board, and The Ugly, Part III

To recap other postings in this series:  my original, Brad Feld’s, Fred Wilson’s first, Fred’s second, Tom Evslin’s, and my lighter-note follow-up.

So speaking of lighter-note takes on this topic, Lary Lazard, Tom Evslin’s fictional CEO who ran Hackoff.com, now has his own tips for effective board management.  You have to read them yourself here, but I think my favorite one is #3, which starts off:

Never number the pages of what you are presenting.  Lots of time can be used constructively figuring out what page everybody is on.

Enjoy.

This is another big week for us at Bolster. On the heels of the announcement we made last month about our Series B financing, we are now announcing the launch of a new program called Bolster Prime and a new venture capital fund called Bolster Ventures. These are important steps in Bolster’s evolution and in the fulfillment of our mission, what we call internally our “Big Idea,” which is to empower the innovation economy.  

The roots of Bolster Prime and Bolster Ventures pre-date the founding of Bolster. In our prior lives, the Bolster founders worked together to scale up a business called Return Path and also 

worked as advisors and mentors to numerous early stage founders and startups. One of the things we noted in our very first post, now part of the About Us section of Bolster.com, was:

After exiting Return Path [the company where our founding team worked for many years], we wanted to do for others what we did for each other as a seasoned executive team. We wanted to know: “How could we help other CEOs, executives and boards bolster themselves to go the distance and scale with their organizations?”

While the founding team was exploring potential business opportunities that allowed us to make a bigger impact on the world, Silicon Valley Bank and High Alpha Innovation were together envisioning a platform to help VC-backed portfolio companies more effectively navigate the complex world of executive talent needs. When our three groups came together, we realized we shared a vision to build a company that puts people first in all aspects to drive high-growth businesses.

I’ve never written before about those other “potential business opportunities” that our team was exploring along with our prior investment syndicate, Fred Wilson from Union Square Ventures, Greg Sands from Costanoa Ventures, and Brad Feld from Foundry. The one our team was particularly excited about was a concept we were calling at the time “Venture Acceleration Partners.” The key points in the pitch deck we created were:

• There is a gap in the market of investors adding “management” value to portfolio companies between Accelerators/Incubators/Studios at the low end and Private Equity firms and very large VCs at the high end. What about the middle?
  
• “The middle” consists of venture-backed companies that are neither early stage nor mature. They are typically founder-led, often by a first-time CEO with new or incomplete management teams who need a lot of mentorship/development, and with a diversified cap table of firms that don’t own operating or consulting practices to help guide the scaling process.
  
• These companies tend to have consistent and stage-unique challenges around scaling execution across every aspect of the business.
  
• By creating an advisory firm made up of seasoned operators, we can quickly identify the risk areas and provide mentoring, guidance and execution to management teams for defined periods of time to keep them on the right track and increase their companies’ performance.
  
• We want to create a firm that has enough skin in the game to have long-term relationships with management teams…and that doesn’t charge (much) for services because incentives are aligned as a co-investor.

Our original deck envisioned a firm that was sort of a hybrid of a “McKinsey for startups” and a venture investor. When I shared that pitch deck (and two other ones I’ll save for another day), with my long-time friend Scott Dorsey from High Alpha, he responded by sharing with me a related pitch deck he was working on with corporate partner Silicon Valley Bank out of the High Alpha Studio for a talent marketplace. We immediately looked at each other and said “we should put all of these ideas together with this founding team, High Alpha and SVB, and the Return Path investors, and change the way startups connect with talent.” That’s what we did, and we almost immediately started building the first part of the Bolster business, which was the talent marketplace.

About six months into our journey building Bolster, I was talking to Brad and reminded him that I was interested in bringing the Venture Acceleration idea to life now that we had a vibrant talent marketplace up and running at Bolster. 

Standing up a new program of this magnitude with limited resources at the same time as building a new venture capital firm from the ground up, on top of a still pretty brand new startup – that felt like a tall order, even for a large and senior founding team like ours. We needed another senior leader to join our team. 

Brad’s visceral response in this conversation was a very clear, “you should hire Jenny.” Enter Jenny Lawton. Jenny is someone I’d known peripherally for many years as a mutual friend and colleague of Brad, but we weren’t particularly close. We agreed to meet for breakfast at a diner halfway between our houses at a time in the pandemic when there wasn’t a whole lot of in-person meetings going on. 

As Jenny’s written about this week, it was the right call at the right time – we had a full meeting of the minds about the role mentorship plays in supporting entrepreneurs, the unmet needs of entrepreneurs even with all the support out there from accelerators and investors, and the desire that both of us had here in the back half of our careers to, as Steve Jobs would say, “make a dent in the universe.” Jenny’s experience as a multiple-time senior executive and startup advisor (including four years as the COO of Techstars) was a perfect match for us. She joined our team pretty quickly, first fractionally (the Bolster way, right?), then full-time in the middle of 2021. 

And the rest, as they say, is history. Working as part of the Bolster leadership team this past year, Jenny has spearheaded the creation of Bolster Prime, from selling and mentoring the first few clients personally, to designing the curriculum and programmatic learning, to figuring out the right positioning and pricing to developing the recruiting strategy for the program. We’ve worked together and along with the rest of the team at Bolster to bring in an amazingly talented group of experienced former and current CEOs and other senior operators as our first group of mentors.  Any entrepreneur would be lucky to have one of these mentors in their corner. We’ve now raised a venture capital fund as first-time fund managers from our own investors and our program’s mentors, all of whom believe in the power of Bolster as the next generation platform to help empower the innovation economy. 

Most good ideas swim in a sea of comparables. There are now a handful of other firms out there that combine advice for entrepreneurs with capital. But we believe our model, with thousands of Bolster Member CXOs already on board, is unique. Bolster Prime and Bolster Ventures, powered by Bolster’s on-demand talent marketplace, is here to help early stage founders reimagine the way they scale up their leadership teams, their boards, and themselves. We are changing the way the startup game is played. Come take a look and see what’s in it for you.

More Useful Than I Thought

I’ve had a Twitter account for a couple years but only started using it in earnest in the last couple of weeks.  And while it is to some extent yet another distraction and flow of information, it’s proving to be much more useful than I thought.  Here are some nuggets from literally less than a week of heavy usage:

– Nice quick exchanges with three existing customers who I otherwise wouldn’t talk to

– Already have over 200 followers, at least 50% just in the last few days

– One set of direct messages, and we turned a skeptic into a free trial provided that the client work with us on an important but difficult case study we’ve been meaning to generate for a while

– One quick @reply later, and I turned someone asking about our services into a live sales call with a local sales team member in London and a positive public tweet back about us

– An exchange with a customer who left us for the competition (partially – he’s still on Sender Score Certified) and said something snarky about us on Twitter yielded a positive tweet and this comment: 

Thanks going out of your way to better understand your customers. That in and of itself means a lot.

– Serendipity – I was on the west coast, noted it, and a friend there pinged me to see if I had time to get together (I didn’t this trip, but that would have been a nice bonus)

– Set up my blog to notify of any new post via Twitter using twitterfeed.com…set up Facebook to pick up my tweets as status updates using the Facebook Twitter app.  The result is that my traffic is WAY up on the blog

I’m sold.  Now I just need to figure out how to be interesting and brief at the same time.

I haven’t taken a poll to figure out the overlap between people who read this blog and people that bought the first edition of Startup CEO, but I’m guessing there’s a high degree of it. If you are familiar with the book, I don’t want to bore you with a recap of what I wrote, but I thought I would devote the next several blogs to new ideas in the second edition. First, the new cover art from the publisher is kind of cool:

The first question you might have is, “Why a second edition? Didn’t you say everything you needed to say the first time?” The answer to that is, yes, I did say everything I had to say at the time, and the first edition is pretty comprehensive as a field guide. But that was about a dozen years into what turned out to be a 20-year journey, and after we sold Return Path in 2019, I had time to reflect on all that happened. I learned a lot of new lessons between the first and second editions, we had a lot of first-time experiences, we scaled the company significantly, and we sold it. None of those things are, in and of themselves, worthy of a second edition, but collectively they help tell the story of startup to exit and tell it from a perspective of creating a sustainable business over nearly two decades. 

But there are other reasons, too, besides new lessons learned. Eight years is a lifetime in terms of changes to micro-trends, language, business in general, and the world around us. I wanted to update the book to make it contemporary so that it can speak to a new generation of CEOs. The second edition is more than a new cover and obvious updates on the number of employees or revenues. I added topics that reflect heightened responsibilities of CEOs around moral and ethical leadership in an increasingly transparent and socially conscious world. How do you navigate a politically charged and divisive society? For example, the State of Indiana passed a law intended to not force people to do things that contravened their religious beliefs but it had the side effect of legal descrimination against LGBT citizens. It was contentious, with rallying cries in business and society for one side or the other, and those same sentiments were found within our employee population. 

How should CEOs handle a situation that conflicts with their core values? There are no easy answers, but avoiding them doesn’t make the problem go away. 

Whether it’s the #metoo movement, high-profile failures of leadership like airline employees dragging customers off of planes, or something as simple as unconscious bias in the workplace, the best CEOs now need to approach their jobs differently. I didn’t write about that in the first edition, but the second edition has an entire chapter devoted to “Authentic Leadership” and provides guidelines and advice to help CEOs. The book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events.

I also added a new section with several chapters on the ins and outs of selling a business. Startup exits are the important culmination of the startup experience and something that the first edition only briefly touched on. Obviously, I was still CEO of a growing company and although we had an opportunity or two to sell within those first years, we never pulled the trigger. The first edition talks about that process at a surface level, but the second edition has far more content and detail since we had completed a sale transaction. 

The first edition of the book has sold close to 40,000 copies as of the writing of the second edition, which blew me away when I tallied it all up. I’ve received many notes of thanks from readers all over the world for the book, and I’m glad that the content has proved useful to so many people, noting from some of the more critical reviews on Amazon that it certainly doesn’t scratch everyone’s itch. I hope the changes in the new edition add even more value to the lives of entrepreneurs and startup management teams. That’s really who the book is written for.

Here are some places to go to pre-order the book:

• Directly from the publisher, Wiley
• From Amazon
• From Books-a-Million
• From Indie Bound 
• From BN.com

I have a limited number of free copies of the book that I can send out, and oddly, they are only print copies since the book publishing ecosystem hasn’t figured out an efficient way for authors to distribute free Kindle copies of books yet.  As a bonus incentive for reading all the way to the end of this post, I will be happy to send a free copy to the first 5 people who comment on this post on the blog and ask for one.

(This is a bonus quick 5th post, inspired by long time StartupCEO.com reader Daniel Clough, to the series that ended last week about Scaling CPO’s- the other posts are: When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer, Signs your Chief Privacy Officer isn’t Scaling, and How I Engage With The Chief People Officer.)

As I’ve noted over the years, the Chief People Officer role is a tough one to get right and a tough one to scale with the organization if what you’re really looking for is a strategic business partner who can lead not just the important blocking and tackling in HR but innovates the people part of your organization, building new systems and programs, approaches recruiting as building great teams instead of filling seats, helps manage your company operating system, and developing and coaching leaders.

A number of later stage CEOs I mentor have come to me over the years when they have a sub-par Chief People Officer and said something like “I’m going to put HR under my CFO.” To me, that’s a bit of a cop-out – it’s acknowledging that the person in the role isn’t strong enough to be a full-throated executive, but the CEO doesn’t want to go through the hassle or expense of replacing them.

Here’s my answer when I hear that from a CEO: “Ok, then your CFO will actually now become your Chief People Officer.  You must have a Chief People Officer on the exec team reporting to you.”

There are few things about which I have a stronger point of view. Someone in your organization must have strategic oversight for human capital. If it’s not your head of HR and you can’t bear recruiting/replacing that person, then it needs to be whoever your put that person under. Or it’s you. But at even mid-scale companies, why would you take that responsibility on yourself?

OnlyOnce, Part II

After more than six years, my blog starting looking like, well, a six-year old blog on an off-the-shelf template.  Thanks to my friends at Slice of Lime, OnlyOnce has a new design as of today as well as some new navigation and other features like a tag cloud and Twitter feed (and a new platform, WordPress rather than Typepad).  I know many people only read my posts via feed or email (those won’t change), but if you have a minute, feel free to take a look.  The site also has its own URL now – https://onlyonceblog.wpengine.com.

With my shiny new template, I may add some other features or areas of content over time, as well.  There are still a couple things that are only 95% baked, but I love the new look and wanted to make if “official” today.  Thanks to Kevin, Jeff, Mike, Lindsay, and everyone at Slice of Lime for their excellent design work, and for my colleague Andrea for helping do the heavy lifting of porting everything over to the new platform.