Aug 142014

How to Manage Your Career

I gave a presentation to a few hundred Return Path employees in January at an all-hands conference we did called “How to Manager Your Career.”

The presentation has three sections — The Three Phases of a Career, How to Get Promoted, and How to Wow Your Manager.

While it’s not as good without the voiceover and interactivity, I thought I’d post it here…see the presentation on Slideshare.

As I said to my audience, if there’s one thing to take away from the topic, it’s this:

Managing your career is up to one, and only one person – you. 

It doesn’t matter how great a corporate culture you have, or how supportive your manager is.  You’re the only person who cares 100% of the time about your career, and you’re the only person with a longitudinal view of what you love, what you’re great at, where you’ve been, and where you want to go.

Mar 202014

Secrets to Yawn-Free Board Meetings

Secrets to Yawn-Free Board Meetings

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I'm publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

The objective of board meetings should always be to have great conversations that help you and your executive team think clearly about the issues in front of you, as well as making sure your directors have a clear and transparent view of the state of the business. These conversations come from a team dynamic that encourages productive conflict. There’s no sure-fire formula for achieving this level of engagement, but here are three few guidelines you can follow to increase your chances.

Schedule board meetings in advance, and forge a schedule that works. Nothing is more disruptive – or more likely to drive low turnout – than last minute scheduling. Make sure you, or your executive assistant, knows board members’ general schedules and travel requirements, and whether they manage their own calendar or have their own executive assistant. Set your board meeting schedule for the year in the early fall, which is typically when people are mapping out most of their year’s major activities. If you know that one of your board members has to travel for your meetings, work with the CEOs of the other companies to coordinate meeting dates. Vary the location of meetings if you have directors in multiple geographies so travel is a shared sacrifice.

In the startup stage of our business at Return Path, we ran monthly meetings for an hour, mostly call-in. In the revenue stage, we moved to six to eight meetings per year, two hours in length, perhaps supplemented with two longer-form and in-person meetings. As a growth stage company, we run quarterly meetings. They’re all in-person, meaning every director is expected to travel to every meeting. We probably lose one director each time to a call-in or a no-show for some unavoidable conflict, but, for the most part, everyone is present. We leave four hours for every meeting (it’s almost impossible to get everything done in less time than that) and sometimes we need longer.

Many years, we also hold a board offsite, which is a meeting that runs across 24 hours, usually an afternoon, a dinner, and a morning, and is geared to recapping the prior year and planning out the next year together. It’s especially exhausting to do these meetings, and I’m sure it’s especially exhausting to attend them, but they’re well worth it. The intensity of the sessions, discussion, and even social time in between meetings is great for everyone to get on the same page and remember what’s working, what’s not, and what the world around us looks like as we dive into the deep end for another year.

Build a forward-looking agenda. The second step in having great board meetings is to set an agenda that will prompt the discussion that you want to have. With our current four-hour meetings, our time allocation is the following:

I. Welcomes and framing (5 minutes)

II. Official Business (no more than 15 minutes unless something big is going on)

III. Retrospective (45 minutes)

a. Target a short discussion on highlighted issues

b. Leave some time for Q&A

IV. On My Mind (2 hours)

a. You can spend this entire time on one topic, more than one, or all, as needed.

b. Format for discussions can vary—this is a good opportunity for breakout sessions, for example.

V. Executive Session (30 minutes)

This is your time with directors only, no observers or members of the management team (even if they are board members).

VI. Closed Session (30 minutes)

This is director-only time, without you or anyone else from the management team.

This agenda format focuses your meeting on the future, not the past. In the early years of the business, our board meetings were probably 75 percent “looking backwards” and 25 percent “looking forwards.” They were reporting meetings—reports which were largely in the hands of board members before the meetings anyway. They were dull as anything, and they were redundant: all of our board members were capable of processing historical information on their own. Today, our meetings are probably ten percent “looking backwards” and 90 percent “looking forwards”—and much more interesting as a result.

Separate background reading and presentation materials. Finally, focus on creating a more engaging dialogue during the meeting by separating background reading from presentation materials. In our early days, we created a huge Powerpoint deck as both a handout the week before the meeting and as the in-meeting deck. That didn’t create an engaging meeting.

There’s nothing more mind-numbing than a board meeting where the advance reading materials are lengthy Powerpoint presentations, than when the meeting itself is a series of team members standing up and going through the same slides, bullet by excruciating bullet—that attendees could read on their own.

When we separated the background and presentation materials, people were engaged by the Powerpoint—because it delivered fresh content. We started making the decks fun and engaging and colorful, as opposed to simple text and bullet slides. That was a step in the right direction, but the preparation consumed twice as much time for the management team, and we certainly didn’t get twice the value from it.

Now we send out a great set of comprehensive reading materials and reports ahead of the meeting, and then we have a completely Powerpoint-free meeting. No slides on the wall. This changes the paradigm away from a presentation—the whole concept of “management presenting to the board”—to an actual discussion. No checking email. No yawns. Nobody nodding off. Everyone—management and board—is highly engaged

Mar 062014

Open Vacation

At Return Path, we’ve had an “open vacation” policy for years, meaning that we don’t regulate the amount of time off people take, and we don’t accrue for it or pay out “unused” vacation if someone leaves the company.  I get asked about this all the time, so I thought I’d post our policy here and also answer a couple follow-up questions I usually get about it.

First, here’s the language of our policy:

Paid Time Off

You’re encouraged to take as much time off as you can while maintaining high performance and achieving your goals. We don’t count the hours you work, so why should we count the hours you don’t? (Unless you’re a non-exempt employee, and only then because we have to!) Take what you need, when you can, and make sure to arrange coverage with your team. If you haven’t had a vacation in a while, you can expect to get a friendly nudge from your manager to get away from the office!

Use your Paid Time Off (PTO) for planned vacations, days off for appointments, religious, or personal holidays that are not offered in your country, community service days, or if you need an unanticipated, last-minute day off to care for a sick child or family member. Statutory or legally protected leaves of absence, such as medical leave, maternity/parental leave, family medical leave or unpaid leave, are governed by separate regulations that will not be affected by our PTO policy. See the Regional section for a list of statutory leaves of absence in your country.

Paid Time Off scheduling is subject to approval by your manager, who has sole discretion to approve or deny requests under this policy. Requests of greater than two consecutive weeks or more than two weeks in one three-month period require approval of your Executive Committee member.

The first question I always get is, “Wow – does that really work?  What issues have you had with it?  My response:

No issues with it at all, other than it’s a little weird to apply internationally, where we have 50 people across 7 countries, since most of those countries have significantly more generous vacation policies/customs than the US.  But we generally make it work.

The second question I get is whether people abuse it or not:

In all the years we’ve done it, we only ever had one person attempt to abuse the policy, one time.  People do still have to ask their managers if it’s ok to take time off, and they do still have to get their jobs done.

Finally, people ask me for general advice on implementing this kind of policy:

Continue to track days off and generate reports for managers every quarter so they at least know whether their people are taking not enough or too much – generally people will take not enough, and you will need to encourage them to take more.  Also, our managers were *really* worried about launching this, so we had to do some hand-holding along the way. 

The results of this policy for us have generally been great.  People take about the same amount of true vacation they used to take, maybe a little more.  They definitely take more half-days and quarter-days where they probably still get a full day worth of work done, without worrying about counting the hours.  Best of all, there’s a strong signal sent and received with this kind of policy that we trust our team members to do what they need to do in order to live their lives AND get their jobs done.

Feb 132014

HR/People Lessons from Netflix

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.

Jan 072014

Startup CEO: The Online Course

As most of you know by now, I wrote a book that was published last fall called Startup CEO:  A Field Guide to Scaling Up Your Business.  I’m excited to announce that, starting on January 20th, the book has now been turned into Kauffman Fellows Academy (KFA) online course called Startup CEO.  Similarly, Brad Feld and Jason Mendelson’s highly successful Venture Deals is also going to launch as Venture Deals KFA online course on February 24th. Both will be offered initially on the NovoEd platform.

The parties involved in getting it off the ground (besides me) were the team at Kauffman Fellows Academy and NovoEd.  Clint Korver, a serial entrepreneur and Stanford adjunct professor, spearheaded the project, and between filming the course and now, he switched jobs from KFA to be the COO at NovoEd, so he has been on all sides of this.   NovoEd is a very unique online educational platform that gives students the ability internationally to work together in teams and collaborate on assignments and peer review one another’s work.  So far over 1,300 people have signed up for Startup CEO from countries as far-flung as the China, Brasil, Iran, the U.K., Australia and, of course, Silicon valley..  This is an exciting extension of the book for me to watch unfold.

The class itself is a very unique format, a bit of “the entrepreneur’s studio” model.  For each chapter of the book (there are 48), I filmed a 5-10 minute Q&A with Clint in front of a live audience of a dozen startup CEOs in New York.  This was a serious production – much more than I expected – with a three-person former CNN production team of Kevin Rockwell, Chuck Afflerbach, and led by former Emmy Award winning CNN Correspondent Rusty Dornin.  Preparing for the class this way was fun and gave me a good opportunity to further crystallize the main point or theme of each chapter.  Having a live audience was super helpful to see what worked and what didn’t work.

Jan 022014

Sabbaticals

I’ve written a few times over the years about our Sabbatical policy at Return Path, including this post and this post about my experience as CEO when one of my direct reports was on his sabbatical, and this post about my own sabbatical.

People ask me this all the time, so I thought I’d write the policy out here.  This is the language in our employee handbook about them:

You have big dreams. We know. This is your chance to cross something off your life list. Whether it’s climbing Mt. Everest, learning Russian or taking your kids across the country in a Winnebago, we believe in rewarding longevity at Return Path and know that a good long break will leave you refreshed and energized!  As such, you are eligible for a sabbatical after your first seven (7) years of employment; then again after every five (5) years incremental employment. The sabbatical provides you with up to six (6) weeks of consecutive time off provided you have that time off approved by your manager at least two months prior to the start of your sabbatical.

You will be requested to sign an Agreement before your sabbatical: if you do not return to work after your sabbatical or if you leave employment within twelve (12) months of returning to work, you will be required to reimburse all amounts received while on sabbatical.  If a holiday occurs on any of of the days of absence, you will not receive holiday pay in addition to your sabbatical pay.  During your sabbatical, your benefits will continue and you will be responsible for making payments for the employee portion of insurance costs if applicable. The period you are on leave will be counted as employment for the purposes of determining your applicable level of benefits.  If you are eligible and have not taken your sabbatical and your employment with Return Path ends (for any reason), you will not be paid out for sabbatical time not taken.

I also wrote an email recently to someone internally that is worth reprinting here, which is How to Prepare for Your Sabbatical, which is aimed at both the person taking the sabbatical, and the person’s manager:

As the employee:

-          Prepare your team

  • Make sure their goals and metrics for your time out are super clear
  • Make sure they know who to go to for what
  • Set their expectations of management coverage (see below). 
  • Remember that your manager has a day job so you should look to see how your team members can take over some of the responsibilities.
  • Give them stretch goals while you’re out

-          Prepare your individual contributor work

  • Hand off all loose ends with extra details. 
  • Make introductions via email if your manager/team member  is going to have to work with external parties
  • Can be to your team, to your manager, to someone else

-          Prepare your manager

  • Brief your manager thoroughly on everything going on with your team, its work, your individual contributor work
  • Good topics to cover with your manager:Discuss specifics of team and 1:1 check-ins and agree on a plan for coverage.
    • What are the big initiatives that you’ll need coverage on
    • Which team members would you like the manager to spend a little extra time with?  Are there any work you would like the manager to help a particular EE with?

-          Prepare yourself

  • Plan any personal travel early so you get good rates!
  • Figure out how to keep your work and personal communications separate – your email (autoresponder, routing, disabling from your smartphone), your voicemail if you use Google Voice or Simulscribe, etc.
  • Block out two full days immediately when you return to catch up on email and catch up with your manager and team

As the manager:

-          Prepare your team

  • Make sure the rest of your team knows your time will be compromised while you’re covering
  • Figure out what kind of coverage you need (either internal or external) while you’re covering

-          Rearrange your calendar/travel

  • Add new team meetings or 1:1s as it makes sense.  You don’t have to do exactly what your employee did, but some portions of it will make sense to pick up
  • If your employee works in another office with members of his/her team, you might want to plan some travel there to cover in person
  • It’s ok to cut back on some other things a bit while you’re covering – just remember to undo everything when the employee’s sabbatical is over

-          While you’re in charge

  • Surprise your employee with how much you were able to keep things running in his/her absence!
  • Learn as much as you can by doing bits and pieces of his/her job.  This is a great opportunity of the employee to get some value from a fresh perspective.

-          Prepare for your employee’s return

  • Keep a running tab of everything that goes on at the company, critical industry news (if appropriate), and with your employee’s function or team and prepare a well-organized briefing document so your employee can hit the ground running when he/she returns
  • Block out an hour or two each of the employee’s first two days back to review your briefing document

 

My main takeaway from this post?  I am overdue my second sabbatical, and it’s time to start thinking about that!

Dec 192013

5 Ways to Get Your Staff on the Same Page

5 Ways to Get Your Staff on the Same Page

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I'm publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s.

To align everyone behind your company’s interests, you must first define and communicate those goals and needs. This requires five steps:

  1. Define the mission. Be clear to everyone about where you’re going and how you’re going to get there (in keeping with your values).
  2. Set annual priorities, goals, and targets. Turn the broader mission into something more concrete with prioritized goals and unambiguous success metrics.
  3. Encourage bottom-up planning. You and your executive team need to set the major strategic goals for the company, but team members should design their own path to contribution. Just be sure that you or their managers check in with them to assure that they remain in synch with the company’s goals.
  4. Facilitate the transparent flow of information and rigorous debate. To help people calibrate the success, or insufficiency, of their efforts, be transparent about how the organization is doing along the way. Your organization will make better decisions when everyone has what they need to have frank conversations and then make well-informed decisions.
  5. Ensure that compensation supports alignment (or at least doesn’t fight it). As selfless as you want your employees to be, they’ll always prioritize their interests over the company’s. If those interests are aligned – especially when it comes to compensation – this reality of human nature simply won’t be a problem.

Taken in sequence, these steps are the formula for alignment. But if I had to single out one as the most important, it would be number 5: aligning individual incentives with companywide goals.

It’s always great to hear people say that they’d do their jobs even if they weren’t paid to, but the reality of post-lottery-jackpot job retention rates suggests otherwise. You, and every member of your team, “work” for pay. Whatever the details of your compensation plan, it’s crucial that it aligns your entire team behind the company’s best interests.

Don’t reward marketers for hitting marketing milestones while rewarding engineers to hit product milestones and back office personnel to keep the infrastructure humming. Reward everybody when the company hits its milestones.

The results of this system can be extraordinary:

  • Department goals are in alignment with overall company goals. “Hitting product goals” shouldn’t matter unless those goals serve the overall health of your company. When every member of your executive team – including your CTO – is rewarded for the latter, it’s much easier to set goals as a company. There are no competing priorities: the only priority is serving the annual goals.
  • Individual success metrics are in alignment with overall company success metrics. The one place where all companies probably have alignment between corporate and departmental goals is in sales. The success metrics that your sales team uses can’t be that far off from your overall goals for the company. With a unified incentive plan, you can bring every department into the same degree of alignment. Imagine your general counsel asking for less extraneous legal review in order to cut costs
  • Resource allocation serves the company, rather than individual silos. If a department with its own compensation plan hits its (unique) metrics early, members of that team have no incentive to pitch in elsewhere; their bonuses are secure. But if everyone’s incentive depends on the entire company’s performance, get ready to watch product leads offering to share developers, unprompted.

This approach can only be taken so far: I can’t imagine an incentive system that doesn’t reward salespeople for individual performance. And while everyone benefits when things go well, if your company misses its goals, nobody should have occasion to celebrate. Everybody gets dinged if the company doesn’t meet its goals, no matter how well they or their departments performed. It’s a tough pill to swallow, but it also important preventive medicine.

Nov 212013

Debunking the Myth of Hiring for Domain Expertise vs. Functional Expertise

Debunking the Myth of Hiring for Domain Expertise vs. Functional Expertise

As a CEO scaling your business, you’ll invariably want to hire in new senior people from the outside.  Even if you promote aggressively from within, if you’re growing quickly enough, you’ll just need more bodies.  And if you’re growing really fast, you will be missing experience from your employee base that you’ll need to augment.

For years, I’ve thought and heard that there’s a basic tradeoff in hiring senior people — you can hire someone with great domain expertise, or you can hire someone with great functional expertise, but it’s almost impossible to find both in the same person, so you need to figure out which is more important to you.  Would I rather hire someone who knows the X business, or someone who is a great Head of X?  Over the course of the last year, I’ve added four new senior executives to the team at Return Path, and to some extent, I’ve hired people with deep functional expertise but limited domain expertise.  Part of that has been driven by the fact that we are now one of the larger companies in the email space, so finding people who have “been there, done that” in email is challenging.

But the amount of senior hiring I’ve done recently has mostly shown me that the “domain vs. functional” framework, while probably accurate, is misleading if you think of it as the most important thing you have to consider when hiring in senior people from the outside.

What’s more important is finding people who have experience working at multiple growth stages in their prior jobs, ideally the scaling stage that you’re at as a business.  It makes sense if you stop and think about it.  If your challenge is SCALING YOUR BUSINESS, then find someone who has DONE THAT before, or at least find someone who has worked at both small companies and larger companies before.  I suppose that means you care more about functional expertise than domain expertise, but it’s an important distinction.

Looking for a new industrial-strength CFO for your suddenly large business?  Sure, you can hire someone from a Fortune 500 company.  But if that person has never worked in a startup or growth stage company, you may get someone fluent in Greek when you speak Latin.  He or she will show up on the first day expecting certain processes to be in place, certain spreadsheets to be perfect, certain roles to be filled.  And some of them won’t be.  The big company executive may freeze like a deer caught in the headlights, whereas the stage-versatile executive will invariably roll up his or her sleeves and fix the spreadsheet, rewrite the process, hire the new person.  That’s what scaling needs to feel like.

Nov 072013

Getting the Most out of Your Investors

Getting the Most out of Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  The first two posts were mine on selecting investors and Fred’s on selecting investments.  This is my second one…and Fred’s post on the other side of the topic is here.

Once you’ve done a venture financing and the smoke clears, you have to transition the relationship you have with your new investor from the courting phase to building a CEO-Director relationship for the long haul.  Here are a few thoughts on how best to do optimize the relationship once it’s established.

  1. Take onboarding seriously.  I always say that the hiring process for new employees doesn’t end when the employee starts…it ends 90 days later after some deliberate onboarding and a two-way review to check in and see how things are going.  Adding a new Board member is the same.  Onboard him or her with some of the same rigor and materials with which you’d onboard a new executive.  Touch base a lot early on.  Schedule an in-person 1:1 check-in after a few months to see how things are going
  2. Give news early and often.  CEOs who wait until Board meetings to share all news are missing out on the point of a good director relationship, as well as missing the point of how communications work in the 2010s.  This is especially true with bad news.  No one likes to get it, but the earlier people hear it, the more they can thoughtfully process it and provide help
  3. Ask for and give feedback early and often.  Though there are certainly some exceptions, venture investors are notoriously bad about giving and receiving feedback.  If you set the tone by asking for feedback regularly – then being sure to internalize and act on it and check back in to see if improvements are obvious – you can get even the most reticent director to speak up.  And there’s no reason you shouldn’t be providing feedback in near-real time as well.  Just because a director is your boss doesn’t mean he or she is meeting your expectations, and it’s a partnership, not a true hierarchical relationship
  4. Ask for help and give assignments.  As a friend of mine says to her kids all the time, You don’t A-S-K, you don’t G-E-T.  If Board members don’t have specific things to work on, they either do nothing, or they do things you don’t need help on.  Drive the work like you would with any team member
  5. Foster independent relationships with your team and other directors.  The hourglass model – where the CEO sits in between the Board and the management team and filters all dialog and data from one group to the other – is outdated.  A director will be much more able to add value to you and to the organization if he or she has an independent point of view as to what’s going on with your team and what other directors are thinking
  6. Encourage directors to speak their minds.  As awful as company politics are, Board politics are worse.  Try to create an environment where directors aren’t shy about saying what’s really on their mind.  You don’t want to get through a Board meeting and then have someone pull you aside and say “what I really think is…”  This means you need to ask them direct questions, not be defensive in your verbal or body-language reaction, and make sure you allow for Executive Sessions at Board meetings
  7. Hold directors accountable.  If you give a Board member an assignment, make sure it gets done on time and the way you asked for it.  If you have a director who is sitting in your Board meetings doing email the whole time, politely (and maybe privately, at least the first time) call him out on it.  If you don’t hold directors accountable, then just like your staff, they will learn that you don’t really mean what you say
  8. Use their time wisely.  No one likes to waste time – certainly not professional investors who sit on a dozen boards.  Get Board materials out early, run productive Board meetings, and while you include some social element like a dinner or outing, make sure even that has the right group and is at the right kind of venue
  9. Augment the Board with independent directors.  Venture directors can be amazingly helpful resources for you and your company.  But they typically have limitations as to their range of operating experience.  If you want to build a great Board and add some counterweights to your VCs, add one or more independent directors who are experienced business operators with experience serving on Boards as well

Year ago when we both first started blogging, Fred and I wrote a whole series of Venture Cliché and Counter-Cliché posts.  Writing these two makes me realize how much fun that was!  I’m looking forward to the class at Princeton next week and to seeing the kinds of questions these four posts inspire.

Oct 312013

Selecting Your Investors

Selecting Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  This is the first one…and Fred’s post on the other side of the topic is here.  Next week, we’ll address the topic of building a successful CEO-VC partnership once it’s established.

If you’re fortunate enough to have built a really strong early stage company, you will find yourself in the position of being able to pick from a number of potential venture investors.  The better your business and the more exciting the space you’re trying to tackle…the more investors you’ll find circling around you.  Here are a few tips for ending up with the best long-term partner as an investor.

  1. Look for VC portfolios that have a lot of “like” companies (B2B, B2C, media, tech, etc.).  One of the strongest points of value that venture investors bring to the table is pattern matching, and you can maximize that by making sure the investor you end up with has seen a multitude of companies like yours
  2. Check references carefully.  Don’t be shy – prospective VCs are checking up on you, and you have every right to do the same with them.  When Fred first invested in Return Path, he gave me a list of every CEO he had ever worked with and said “Call anyone you want on the list.  Some of these guys I worked well with, a couple I fired.  But they’ll all tell you what I’m like to work with.”  First prize is the VC who volunteers this information.  Second prize is the VC who gives it to you when you ask.  A distant third price is the VC who gives you two names and ask for time to prep them ahead of time
  3. Focus on the person first, the firm second.  Having a good venture firm is important.  But at the end of the day, you’re dealing with a person first and foremost.  That’s who will be on your board giving you advice and measuring your performance.  Better to have an A person at a B firm than a B person at an A firm (of course, even better to have an A person at an A firm).  This means two things – selecting a great person to be on your Board, and also making sure you end up with a person who has enough juice within his or her firm to get things done on your behalf with the partnership
  4. 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 this is true of any negotiation, not just a term sheet.  It’s often said that good choices come from good options. Sometimes, you have to walk away from a deal where you’ve invested a lot of time, energy, and emotion.  But as an entrepreneur, you can mitigate the number of times you have to walk away by developing good alternative options to a particular deal. That way, if one option doesn’t pan out as you’d hoped, another very good option is waiting in the wings.  If you negotiate with two or three VCs, you’ll have a great backstop and won’t let the emotional investment in the deal get the best of you.  Yes, you will spend twice to three times the amount of time on the process, but it’s well worth it
  5. Don’t be swayed by promises of help.  I’ve heard VCs say it all.  They’ll help you fill out your management team.  They’ll get you customers.  They’ll help with your back office.  They’re loaded up with value-add.  If venture investor has staffed his or her firm with support personnel who are available free of charge to portfolio companies (this does happen once in a while), then assume your VC will be as helpful as possible, but no more or less helpful than another investor
  6. Handle the negotiation yourself, in person as much as possible.  The best way to get to know someone’s character is to negotiate a deal with him.  This gives you lots of opportunities to look for reasonableness, and to see if he or she is able to focus on the big picture.  The biggest warning sign to look for is someone who says things like “you have to agree on this term, because this is how we always do deals.”  By the way, how you handle yourself in this negotiation is equally important.  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
  7. “Pay up” for quality and for a clean security.  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).  Similarly, I’d always 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 percent of your company or 30 percent of your company is much less important than having a capital structure that’s easy for an outsider to understand and want to join

As with all things, there are probably another dozen items that could be added to this list, but it’s a good starting point.  However, your more important role as CEO is to put your company in a position where you can select from a number of high quality investors, so start there!

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