Why I joined the DMA Board, and what you can expect of me in that role
Why I joined the DMA Board, and what you can expect of me in that role
I don’t normally think of myself as a rebel. But one outcome of the DMA’s recent proxy fight with Board member Gerry Pike is that I’ve been appointed to the DMA’s Board and its Executive Committee and have been labeled “part of the reform movement” in the trade press. While I wasn’t actively leading the charge on DMA reform with Gerry, I am very enthusiastic about taking up my new role.
I gave Gerry my proxy and support for a number of reasons, and those reasons will form the basis of my agenda as a DMA Board member. As a DMA member, and one who used to be fairly active, I have grown increasingly frustrated with the DMA over the past few years.
1. The DMA could be stronger in fighting for consumers’ interests. Why? Because what’s good for consumers is great for direct marketers. Marketing is not what it used to be, the lines between good and bad actors have been blurred, and the consumer is now in charge. The DMA needs to more emphatically embrace that and lead change among its membership to do the same. The DMA’s ethics operation seems to work well, but the DMA can’t and shouldn’t become a police state and catch every violation of every member company. Its best practices and guidelines take too long to produce and usually end up too watered down to be meaningful in a world where the organization is promoting industry self-regulation. By aggressively fighting for consumers, the DMA can show the world that a real direct marketer is an honest marketer that consumers want to hear from and buy from.
2. Despite a number of very good ideas, the DMA’s execution around interactive marketing has been lacking. The DMA needs to accept that interactive marketing IS direct marketing – not a subset, not a weird little niche. It’s the heart and soul of the direct marketing industry. It’s our future. The acquisition of the EEC has been one bright spot, but the DMA could do much more to make the EEC more impactful, grow its membership, and replicate it to extend the DMA’s reach into other areas of interactive marketing, from search to display advertising to lead generation. The DMA’s staff still has extremely limited experience in interactive marketing, they haven’t had a thought leader around interactive on staff for several years, and their own interactive marketing efforts are far from best practice. Finally, the DMA’s government affairs group, perhaps its greatest strength, still seems disproportionately focused on direct mail issues. The DMA should maintain its staunch support of traditional direct marketers while investing in the future, making interactive marketing an equal or larger priority than traditional direct marketing. We have to invest in the future.
3. Finally, I think the DMA suffers from a lack of transparency that doesn’t serve it well in the hyper-connected world we live in here in 2009 – that’s a nice way of saying the organization has a big PR problem. The organization does a lot of great work that never gets adequately publicized. This whole proxy fight episode is another example, both in the weak response from the DMA and also in a lot of the complaints Gerry lodged against the organization, many of which the organization says are untrue or misleading. Senior DMA execs or Board members should be blogging. They should be active thought leaders in the community. They should be much more engaged with their members to both understand member needs and requirements and more aggressively promote their agenda.
In short, I will be an independent voice who advocates for progress and change in the areas that I consider to be most important, and I will be transparent and open about expressing my views. I’ve already been clear with the existing DMA Board and management that I do have this agenda, and that I hope the organization will embrace it. If they do, even if only in part, I think it will be to the DMA’s benefit as well as the benefit of its members. If they reject it wholesale, my interest in long-term involvement will be fairly low.
That’s the story. As I said up front, I am taking up this new role with enthusiasm and with the belief that the DMA is open to change and progress. We’ll see how it goes, and I will blog about it as often as I can.
Do you have thoughts on the future of the DMA? I’d love to hear from you. You can leave a comment below or email me directly at matt at returnpath dot net.
Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline
Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline
As I mentioned a few weeks ago here, I’m excited to be writing a book called Startup CEO: A Field Guide to Building and Running Your Company, to be published by Wiley & Sons next summer. Since many readers of OnlyOnce are my target audience for the book, I thought I’d post my current outline and ask for input and feedback on it. So here it is, still a bit of a work in progress. Please comment away and let me know what you think, what’s missing, what’s not interesting!
1Â Â Â Â Â Â Â Â Â Â Part One: Vision and Strategy (Defining the Company)
1.1         Setting the Company’s Agenda
1.2         NIHITO! (or, “Nothing Interesting Happens in the Office”)
1.3Â Â Â Â Â Â Â Â Â Setting the Business Direction
1.4Â Â Â Â Â Â Â Â Â Strategic Planning, Part I: Turning Concepts Into Strategy
1.5Â Â Â Â Â Â Â Â Â Strategic Planning, Part II: Creating the Plan
1.6Â Â Â Â Â Â Â Â Â Defining Mission, Vision and Values
1.7Â Â Â Â Â Â Â Â Â Communicating Vision and Strategy
1.8Â Â Â Â Â Â Â Â Â The Role of M&A
1.9Â Â Â Â Â Â Â Â Â The Art of the Pivot
1.10Â Â Â Â Â Â How Vision and Strategy Change over Time
2          Part Two: Talent (Building the Company’s Human Capital)
2.1Â Â Â Â Â Â Â Â Â Building a Team
2.2Â Â Â Â Â Â Â Â Â Scaling the Team
2.3Â Â Â Â Â Â Â Â Â Culture
2.4Â Â Â Â Â Â Â Â Â Interviewing
2.5Â Â Â Â Â Â Â Â Â Recruiting
2.6Â Â Â Â Â Â Â Â Â Onboarding
2.7Â Â Â Â Â Â Â Â Â Setting Goals
2.8Â Â Â Â Â Â Â Â Â Feedback
2.9Â Â Â Â Â Â Â Â Â Development
2.10Â Â Â Â Â Â Compensation
2.11Â Â Â Â Â Â Promoting
2.12Â Â Â Â Â Â Rewarding
2.13Â Â Â Â Â Â Managing Remote Offices and Employees
2.14      Firing: When It’s Not Working
2.15Â Â Â Â Â Â How Talent Changes over Time3Â Â Â Â Â Â Â Â Â Â Part Three: Execution (Aligning Resources with Strategy)
3.1         Making Sure There’s Enough Money in the Bank
3.2Â Â Â Â Â Â Â Â Â Types of Financing
3.3Â Â Â Â Â Â Â Â Â Fundraising Basics
3.4Â Â Â Â Â Â Â Â Â Negotiating Deals
3.5Â Â Â Â Â Â Â Â Â Pros and Cons of Outside Financing
3.6Â Â Â Â Â Â Â Â Â Forecasting and Budgeting
3.7Â Â Â Â Â Â Â Â Â Creating a Company Operating System
3.8Â Â Â Â Â Â Â Â Â Meeting Routines
3.9Â Â Â Â Â Â Â Â Â Driving Alignment
3.10Â Â Â Â Â Â A Metrics-Driven Approach to Running a Business
3.11Â Â Â Â Â Â Learning
3.12Â Â Â Â Â Â Post-Mortems
3.13Â Â Â Â Â Â Thinking About Exits
3.14Â Â Â Â Â Â How Execution Changes over Time
3.14.1Â Â Â Â Â Finance
3.14.2Â Â Â Â Â Execution4Â Â Â Â Â Â Â Â Â Â Part Four: Management And Leadership (The How of Being a CEO)
4.1Â Â Â Â Â Â Â Â Â Leading an Executive Team
4.2Â Â Â Â Â Â Â Â Â Critical Personal Traits
4.3Â Â Â Â Â Â Â Â Â Being Collaborative
4.4Â Â Â Â Â Â Â Â Â Being Decisive: Balancing Authority and Consensus
4.5Â Â Â Â Â Â Â Â Â The Value of Symbolism
4.6Â Â Â Â Â Â Â Â Â Getting the Most out of People
4.7Â Â Â Â Â Â Â Â Â Diving Deep without Being Disruptive
4.8Â Â Â Â Â Â Â Â Â Articulating Purpose
4.9Â Â Â Â Â Â Â Â Â Collecting Data from the Organization
4.10Â Â Â Â Â Â Managing in an Economic Downturn
4.11Â Â Â Â Â Â Managing in Good Times vs. Bad Times
4.12Â Â Â Â Â Â Communication
4.12.1Â Â Â Â Â Macro (to Your Company and Customers)
4.12.2Â Â Â Â Â Micro (One-on-One)
4.13      How Management and Leadership Change over Time5          Part Five: Boards (A Unique Aspect of the CEO’s Job)
5.1Â Â Â Â Â Â Â Â Â Building Your Board
5.2Â Â Â Â Â Â Â Â Â Meeting Materials
5.3Â Â Â Â Â Â Â Â Â Meetings
5.4Â Â Â Â Â Â Â Â Â Between Meetings
5.5Â Â Â Â Â Â Â Â Â Making Decisions and Maximizing Effectiveness
5.6Â Â Â Â Â Â Â Â Â The Social Aspects of Running a Board
5.7Â Â Â Â Â Â Â Â Â Working with the Board on Compensation
5.8Â Â Â Â Â Â Â Â Â Evaluating the Board
5.9Â Â Â Â Â Â Â Â Â Serving on Other Boards
5.10Â Â Â Â Â Â How Boards Change over Time6Â Â Â Â Â Â Â Â Â Â Part Six: Managing Yourself So You Can Manage Others
6.1Â Â Â Â Â Â Â Â Â Creating a Personal Operating System
6.2Â Â Â Â Â Â Â Â Â Working with an Executive Assistant
6.3Â Â Â Â Â Â Â Â Â Working with a Coach
6.4Â Â Â Â Â Â Â Â Â Finding Your Voice
6.5Â Â Â Â Â Â Â Â Â The Importance of Peer Groups
6.6Â Â Â Â Â Â Â Â Â Your Family
6.7Â Â Â Â Â Â Â Â Â Taking Stock
6.8Â Â Â Â Â Â Â Â Â Staying Fresh
6.9Â Â Â Â Â Â Â Â Â Staying Healthy
6.10Â Â Â Â Â Â Traveling
Book Shorts: Fred the Cow?
Book Shorts:Â Fred the Cow?
I enjoyed two interesting, super-quick reads from last week that have a common theme running through them:Â being remarkable.
The Fred Factor, by Mark Sanborn, is one of those learn-by-storytelling business novellas. It’s all about the author’s mailman, Fred, and how Fred has figured out how to make a difference in people’s lives even with a fairly routine job. The focal points of the book are things like “practice random acts of kindness” and “turn the ordinary into the extraordinary by putting passion into your work.” It’s a good reminder that it is unbelievably easy, not to mention free, to be kind and thoughtful, and that those things are always always always worth doing. Kinda makes me wonder what the Brad factor is. <g>
The Big Moo, a collection of essays written by 33 different business thinkers/writers and edited by Seth Godin, isn’t out yet, but you can pre-order it via that link on Amazon. It follows the main theme of another of Seth’s books, Purple Cow, about how to make your business remarkable and backs it up with various vignettes from the different writers. It has some great reminders about how easy and inexpensive it can be to be remarkable in business. Wisdom like “Criticism? Internalize it,” and “Get great ideas about your business from new employees,” and “How would you run your business if you relied on donations from your customers in order to survive?” are all insightful and thought provoking.
Each is great and an easy read, and while one is more personal and the other business-oriented, in they are both somewhat remarkable.
More Good Inc.
More Good Inc.
Last year I was pleased and proud to write about our debut on the Inc. 500 list of America’s fastest growing companies. At that time I wrote that “Now our challenge, of course, is STAYING on the list, and hopefully upping our ranking next year!” Well, I am again please and proud to announce that we, in fact, stayed on the list. (You can read all the Inc. coverage here and see our press release about the ranking here.)
Unfortunately, we didn’t make the second part of our goal to up our rank. But, we did up our growth – our three-year revenue growth rate was 18% higher than last year. This is a testament to the hard work of our team (now 150 strong!) and wouldn’t be possible without the support of our many great clients (now 1,500 strong!). Most importantly, we see no end in sight. In fact, 2008 promises to be an even bigger year for us as we poise for continued growth. By the way, would you like to be part of a team that has now ranked as one of America’s fastest growing companies two years in a row? Check out our Careers page and join the team that is advancing email marketing, one company at a time.
Please, Keep Not Calling (Thank You!)
Please, Keep Not Calling (Thank You!)
It’s been three years since the federal government passed one of its better pieces of legislation in recent memory, creating the Do Not Call Registry which is a free way of dramatically reducing junk phone solicitations. At the time, registrations were set to expire every three years. When I signed up my phone number, I stuck a note in my calendar for today (three years later) to renew my registration. I was planning on blogging about it to remind the rest of the world, too.
To my great surprise, when I went to the site today, I saw this note:
Your registration will not expire. Telephone numbers placed on the National Do Not Call Registry will remain on it permanently due to the Do-Not-Call Improvement Act of 2007, which became law in February 2008.
That’s two great pieces of legislation. What will they think of next?
Introducing Bolster Prime and Bolster Ventures (and their back story)
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. Â
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.Â
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.
Email Intelligence and the new Return Path
Welcome to the new Return Path.
For a tech company to grow and thrive in the 21st century it must be in a state of constant adaptation. We have been the global market leaders in email deliverability since my co-founder George Bilbrey coined that term back in 2002. In fact, back in 2008 we announced a major corporate reorganization, divesting ourselves of some legacy businesses in order to focus on deliverability as our core business. Â
 Since then Return Path has grown tremendously thanks to that focus, but we have grown to the point where it’s time for us to redefine ourselves once again. Now we’re launching a new chapter in the company’s history to meet evolving needs in our marketplace. We’re establishing ourselves as the global market leaders in email intelligence. Read on and I’ll explain what that means and why it’s important.
What Return Path Released Today
We launched three new products today to improve inbox placement rate (the new Inbox Monitor,  now including subscriber-level data), identify phishing attacks (Email Brand Monitor), and make it easier to understand subscriber engagement and benchmark your program against your competition (Inbox Insight, a groundbreaking new solution). We’ve also released an important research study conducted by David Daniels at The Relevancy Group.
The report’s findings parallel what we’ve been hearing more and more recently. Email marketers are struggling with two core problems that complicate their decision making: They have access to so much data, they can’t possibly analyze it fast enough or thoroughly enough to benefit from it; and too often they don’t have access to the data they really need.
Meanwhile they face new challenges in addition to the ones email marketers have been battling for years. It’s still hard to get to the inbox, and even to monitor how much mail isn’t getting there. It’s still hard to protect brands and their customers from phishing and spoofing, and even to see when mail streams are under attack. And it’s still hard to see engagement measurements, even as they become more important to marketing performance.
Email Intelligence is the Answer
Our solution to these problems is Email Intelligence. Email intelligence is the combination of data from across the email ecosystem, analytics that make it accessible and manageable, and insight that makes it actionable. Marketers need all of these to understand their email performance beyond deliverability. They need it to benchmark themselves against competitors, to gain a complete understanding of their subscribers’ experience, and to accurately track and report the full impact of their email programs. In fact, we have redefined our company’s mission statement to align with our shift from being the global leader in Email Deliverability to being the global leader in Email Intelligence:
We analyze email data and build solutions that generate insights for senders, mailbox providers, and users to ensure that inboxes contain only messages that users want
The products we are launching today, in combination with the rest of our Email Intelligence Solution for Marketers that’s been serving clients for a decade, will help meet these market needs, but we continue to look ahead to find solutions to bigger problems. I see our evolution into an Email Intelligence company as an opportunity to change the entire ecosystem, to make email better, more welcome, more effective, and more secure.
David’s researchoffers a unique view of marketers’ place in the ecosystem, where they want to get to, how much progress they’ve made, and how big a lead the top competitors have opened up against the rest. (It can also give you a sense of where your efforts stack up vs. the rest of the industry.) There are definitely some surprises, but for me the biggest takeaway was no surprise at all: The factors that separate the leaders are essentially the core components of what we define as Email Intelligence.
Startup CEO: The Online Course Part II
Startup CEO: The Online Course Part II
Startup CEO the online course offered by the Kauffman Fellows Academy is back this fall starting September 15! As many of you know, the course is based on my book Startup CEO: A Field Guide to Scaling Your Business.
When the course first ran earlier this year, I wasn’t sure what to expect. Hundreds of students from six continents signed up, all eager to learn as much as they could about entrepreneurship and how to develop their startups. The students worked together in teams to develop their startup ideas on the unique online educational platform NovoEd. I was amazed at the enthusiasm of students who dove into lectures and the book and then exchanged ideas in the forums. It was very powerful to see cohorts of students from all over the world sharing their experiences together, almost like the CEO peer group that I write about in the book.
The real power of it really hit me when I was in Brazil  this last spring at a dinner and one of the attendees approached me and told me he was one of the Startup CEO students and how much he was enjoying the course.
To bring the class to life, we began holding Google hangouts moderated by KFA VP and former CNN correspondent Rusty Dornin. The students could write in questions live during the hangout or watch the recorded version later. The hangouts were not only informative but fun.
Here are a few comments from students in the winter course:
“The lectures and the hangouts were incredibly insightful. I’m sure I’ll avoid a good number of mistakes I would have surely made without taking this class!
“I enjoyed the high quality of the lecturers and their very practical experience and guidance. This included the excellent visiting lecturers and whilst I was unable to join the hangouts in real time (I’m in Australia) I was able to watch the recordings”
In addition, Brad Feld and Jason Mendelson’s course Venture Deals based on their popular book Venture Deals: Be Smarter than Your Lawyer and Venture Capitalist will begin September 29th. Brad Feld and other celebrated investors will also be featured in hangouts for the course and Brad loves to dive into the forums.
I am looking forward to this next round and our global discussion of how to create and manage successful startups.
How to Negotiate a Term Sheet with a VC (Updated)
This is another in a series of postings that relate to Fred’s and Brad’s various postings about venture capital funding. (Please note I have added an 11th item in response to a comment by Jack Sinclair, Return Path’s VP of Finance and my partner in crime on all transactions for the past five years.)
I think the most important part of the venture financing process is negotiating the term sheet. Although they’re only 2-3 pages long, term sheets contain summaries of all the critical aspects of a financing, and once they’re signed, the remainder of the financing process is significantly more “automatic.” Based on the financings I’ve seen and worked on – both as a VC and as an entrepreneur – my Top 10 (now 11) biggest takeaways for entrepreneurs are as follows (not in any particular order):
1. Get a good lawyer. I mean a really good one. Not just one who you are comfortable with and who is productive and doesn’t charge you too much (as Brad says, your wife’s brother’s friend’s neighbor), but one who knows venture financings like the back of his or her hand. They’re out there, many of them have worked on both sides of these transactions – for VCs and for entrepreneurs, and they can save your ass. No matter how many deals you’ve worked on, your lawyer has worked on more of them. Return Path’s lawyer, David Albin from Finn Dixon & Herling, is great if you need one.
2. Focus on terms that matter, otherwise known as Pick your battles. A typical VC term sheet will have at least 20 terms spelled out in it. There are only a few that really matter in the end, although you should at least make sure your lawyer is comfortable that the others are reasonable and somewhat standard. Spend time on valuation, the type of security, the option pool, Board composition, and your own compensation and rights.
2a (new). Sacrifice valuation for a clean security. Everyone always thinks that price/valuation is the most important thing to maximize in a deal. However, the structure of the security can be much more important in the long run. Whether the VCs buy 33% of your company or 30% of your company is much less important than having a capital structure that’s easy for an outsider to understand and want to join (e.g., investment banker or later-stage VC).
3. Always have a BATNA (Best Alternative to a Negotiated Agreement – a fancy way of saying Plan B). This is probably the most important piece of advice I can offer, and it extends to any negotiation, not just term sheets. If you have two or three VCs who are interested in funding you, I can guarantee you will end up with better terms from the highest quality investor in the group if you play the negotiation well. If you have one term sheet, you have zero leverage in your negotiation. Yes, you will spend 2-3x the amount of time on the process, but it’s well worth it.
4. Be prepared to pay up for high quality investors. There is a world of difference between good VCs and bad VCs (both the individual partners and the firms) that will ultimately have a lot to do with how successful your company can become. The quality of your VC isn’t more important than the quality of your product or your team, but it’s right up there. But – and this is an important but – you should expect to “pay” for quality in the form of slightly weaker terms (whether valuation or type of security). This is where having a BATNA really comes in handy.
5. Ask for references. Don’t be shy – prospective VCs are checking up on you…you have every right to do the same with them. Ask them for references of CEOs they’ve worked with. Ask them for a CEO they’ve had to fire as a reference. The good ones will give you the full roster of everyone they’ve ever funded and tell you to call anyone. The bad ones will give you two names and ask for time to prep them ahead of time.
6. Don’t let the VC get away with negotiating a point by saying “we always do it this way.” That’s just not true. VCs may have a preferred way of doing deals or handling a specific term, but every deal they’ve ever done is different, and they know it. If there’s a compelling reason for them to insist on a particular term, you have the right to hear it (if it’s important to you).
7. If you have multiple investors in the syndicate, insist on a single investor counsel and a lead investor. This is essential to (a) protect your sanity, and (b) prevent you from paying zillions of dollars in legal fees. You have to make the VCs stick to it, though – they can’t come back and re-trade the deal after it’s been negotiated. This is also helpful in getting a syndicate cooperating with each other and aligning the members’ interests, particularly if it has investors who have participated in different rounds of the company’s financing. Do expect to play moderator constantly throughout the process, however, to ensure that it goes smoothly.
8. Try do deal in advance with follow-on financings. When an investor doesn’t participate in a follow-on financing, it creates a total nightmare for you. Other investors will want to punish their wayward colleague and can create massive collateral damage in the process to common shareholders and management. Just as VCs will insist on something called “pre-emptive rights” (the right to invest in future financings if they want), you and your lawyer should insist on some protection in the event that one of your investors abandons you when you are raising more capital.
9. Handle the term sheet negotiation carefully. Whether it’s an initial round or a follow-on round, how you handle yourself in this negotiation sets the tone for the next stage of your relationship with the VC. The financing is the line of demarcation between you and the VC courting each other, and the VC joining your board and effectively becoming your boss.
10. Finally don’t forget to say thank you at the end of the process. Whether you send a formal email, a handwritten note, or a token gift, be sure to thank your VCs after a financing. They’re putting their butt on the line for your company, they’re investing in YOU, and they’re making it possible for you to pursue your dream. That deserves a thoughtful thanks in my book.
Sorry for the long posting. The next one or ones in this series will be on valuation, preferences, and “Venture Capital deal algebra.”
Startup CEO, Second Edition
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.
The Art of the Quest
Jim Collins, in both Good to Great and Built to Last talked about the BHAG – the Big, Hairy Audacious Goal – as one of the drivers of companies to achieve excellence. Perhaps that’s true, especially if those goals are singular enough and simplified enough for an entire company of 100-1000-10000 employees to rally around.
I have also observed over the years that both star performers and strong leaders drive themselves by setting large goals. Sometimes they are Hairy or Audacious. Sometimes they are just Big. I suppose sometimes they are all three. Regardless, I think successfully managing to and accomplishing large personal goals is a sign of a person who is driven to be an achiever in life – and probably someone you want on your team, whether as a Board member, advisor, or employee, assuming they meet the qualifications for the role and fit the culture, of course.
I’m not sure what the difference is between Hairy and Audacious. If someone knows Jim Collins, feel free to ask him to comment on this post. Let’s assume for the time being they are one and the same. What’s an example of someone setting a Hairy/Audacious personal goal? My friend and long-time Board member Brad Feld set out on a quest 9 years ago to run a marathon in each of the 50 states by the age of 50. Brad is now 9 years in with 29 marathons left to go. For those of you have never run a marathon (and who are athletic mortals), completing one marathon is a large, great and noteworthy achievement in life. I’ve done two, and I thought there was a distinct possibility that I was going to die both times, including one I ran with Brad . But I’ve never felt better in my life than crossing the finish tape those two times. I’m glad I did them. I might even have another one or two in me in my lifetime. But doing 50 of them in 9 years? That’s a Hairy and Audacious Goal.
For me, I think the Big goal may be more personally useful than the Hairy or Audacious. The difference between a Big goal and a Hairy/Audacious one? Hard to say. Maybe Hairy/Audacious is something you’re not sure you can ever do, where Big is just something that will take a long time to chip away at. For example, I started a quest about 10-12 years ago to read a ton of American history books, around 50% Presidential biographies, from the beginning of American history chronologically forward to the present. This year, I am up to post-Civil War history, so roughly Reconstruction/Johnson through Garfield, maybe Arthur. I read plenty of other stuff, too – business books, fiction, other forms of non-fiction, but this is a quest. And I love every minute of it. The topic is great and dovetails with work as a study in leadership. And it’s slowly but surely making me a hobby-level expert in the topic. I must be nearing Malcolm Gladwell’s 10,000 hours by now.
The reason someone sets out on a personal quest is unclear to me. Some people are more goal-driven than others, some just like to Manage by Checklist, others may be ego-driven, some love the challenge. But I do think that having a personal quest can be helpful to, as Covey would say, Sharpen the Saw, and give yourself something to focus personal time and mental/physical energy on.
Just because someone isn’t on a personal quest doesn’t mean they’re not great, by the way. And someone who is on a quest could well be a lunatic. But a personal quest is something that is useful to look for, interesting and worth learning more about if discovered, and potentially a sign that someone is a high achiever.