Sponsor Posts

Thanks to George Zachary, a partner at Charles River Ventures, for sponsoring Venture Hacks this week. If you like this post, check out George’s blog and tweets @georgezachary. – Nivi

In my first post, A brief history of your investors (and their investors), I wrote about the history of venture capital. I described how the economy and stock market drives investments into venture capital and startups. I also covered how the basic incentive structures are affected by these drivers.

I ended with a suggestion that cash is gaining power relative to other assets and a suggestion that this will shift the balance of valuation and terms in favor of the root sources of capital (limited partners and above). In this second part, I’ll discuss why I think this is happening and what it means for venture investors and entrepreneurs.

Speculative returns are a major component of total returns

The coming decade is not going to be a bull like the 1980’s or 1990’s. Why is this important? Because it’s going to turn money into a “scarce” commodity and therefore drive down valuations, erode returns, remove under-performing venture funds, and reduce company exit valuations.

The 1980’s and 90’s were incredibly bullish. The annualized return from the public stock market was 16.8% from 1982-2000. That is huge. If you dive into the 16.8%, the fundamental return was 9.9% annualized.

What’s the remainder? I’ll call it speculative return. The speculative return was 6.9% between 1982-2000. And what is speculative return? It’s the expansion of the starting and ending P/E from 1982 to 2000. We started 1982 with a P/E of 8.0 and finished 2000 at 26.4!

As I wrote in part one, the increased supply of money drove these large returns. M3 money supply started its ballistic rise in the early 1980s. The total debt market went from $4T in 1980 to about $52T at the end of 2009. So the credit boom and decreasing interest rates fire-hosed cash into all markets. And that’s how a speculative return of 6.9% a year was driven. Other drivers included the baby boomer demographic, the technology boom, geopolitical stability, and the boom in international trade from globalization.

If we look back in time, the preceding time period of 1966 to 1981 had a total return of 5.9% (including dividends of course). However, the fundamental return was 11.1% and the speculative return was -5.2%! We started 1966 with a P/E of 17.8 and finished 1981 with a P/E of 8.0. And to add a little more color, the 1950-1965 post-WWII time period had a total return of 16.1%. That was comprised of a 10.0% fundamental return and a 6.1% speculative return. And, looking forward a bit, we can see the 2001-2005 time period had a total return of -1.3% with a -6.9% speculative return.

This data suggests that the speculative return component is a huge driver on total returns. And that it has a fairly long half-cycle time. It’s in the vicinity of 16-18 years if we do the analysis since the early 1900s. In a short 5 year period, speculative return can comprise 55% of the total return. And, over a 40 year period, speculative return drops to near 0%.

Benjamin Graham said it best when he said that the stock market worked like a voting machine, but in the long term like a weighing machine. If you are building a long term company, that is the good news. The not-so-good news is that the short term pain of being part of the voting machine could be very significant.

2001-2020 will have negative speculative returns

Okay, its 2010. Could the speculative return dynamics since 2001 have ended? Umm — probably not. Take a look at this table of important drivers that compare 1981 (the start of the mega 20 year bull period) to now.

1981 Today
CPI 8.9% -1.3%
30-year bond 13.65% 4.24%
Fed Funds rate 12.00% 0.25%
Highest marginal tax rate 69% 35%
Highest LT capital gains tax rate 28% 15%
Home ownership rate 65.2% 67.4%
Household debt as % of income 56.1% 114.4%
% of families with retirement accts 20.4% 52.6%
Personal savings rate 11.4% 3.0%
Mortgage debt as % of disposable inc 43.1% 95%
Baby Boomer age range 17-35 45-63
Federal Deficit as % of Nominal GFP 2.5% 11.2% est
PCE (consumer spend) as % of GDP 61.9% 70.7%
US debt as % of GDP 32.2% 85.8%
Household debt as % of GDP 47.2% 96.8%

To me, these are very sobering statistics. They paint a completely different picture than at the start of the last bull cycle of 1982-2000. My judgment is that these statistics are going to seriously suppress speculative return. The -6.9% of 2001-2005 will get worse and total returns will suffer. In 2021, statistics will show that the 2001-2020 time period had good fundamental returns. But horrific speculative returns.

Valuations go down and diligence goes up for startups and VCs

What will this mean for the U.S. entrepreneurs and investors? In short, we are not going to be “partying like its 1999” for quite awhile. (Who knew that the artist formerly known as Prince could forecast market peaks?)

The implications of negative speculative returns will be huge. The number of venture firms and their personnel will shrink. And probably hit bottom sometime this decade. Venture firms will be under significant pressure to outperform their peers and outperform their limited partners’ common benchmark indices like NASDAQ. Limited partners will feel the same type of pressure as they too source their capital from sources that will be under tremendous economic pressures. Angel firms (translation: angels who are institutionally backed) will feel the same pressure. Angel investors (individuals investing their own capital) will become more risk averse.

How will these pressures affect entrepreneurs? As a whole, valuations will stay suppressed and will probably come down further over the future years. Revenue multiples and “discount to public market multiples” will re-enter and dominate the late stage financing lexicon. Early stage companies will also feel this suppression with smaller venture rounds. Capital-intense startups that need to raise large initial Series A financing rounds will be particularly affected.

The amount of time spent in due diligence will go up and get more rigorous and detailed. Of course, there will always be companies that are exceptions. But as a rule, the suppressed return environment will force all parts of the money chain to spend way more time in diligence. Way more time and energy for limited partners to raise capital. And the same for venture investors. And the same for angel firms.

Startups will feel this diligence pressure next as they are the next stop on the money supply chain. My guess is that new service providers will emerge to help both investors and entrepreneurs with these diligence processes. How they will be paid is an open question.

Since individual angels use their own cash, they won’t be directly affected. But they will probably diversify their portfolio by making smaller investments on average. And put less of their total portfolio in startups so that they can have greater portfolio liquidity. In aggregate, they will put less money into startups.

Some startups and VCs are going to disappear

Okay, so valuations down and diligence up for every part of the money supply chain. We can all work through that.

Where matters are going to get tricky is that parts of the money supply chain will disappear. A venture investor or angel firm may run out of cash in a fund and need to raise a new fund. A startup company has a similar problem.

If you are a startup company, a pure non-dilutable asset is your time. Raising a new financing round requires time. Since we’ve already established that investor due diligence time will increase, the last thing an entrepreneur will want to do is spend that time talking with investors who don’t have cash to invest. Or who can only invest with particularly harsh terms because of their own liquidity needs.

In the next and final part of this series, I will detail the questions you should ask your potential investors. These questions will assist you in ensuring you are talking to the right investors for your company.

In closing, here’s the “New York Daily Investment News” front page from the early part of the Great Depression to remind us that history may not repeat exactly. But it does rhyme.

Thanks to KISSmetrics for supporting our interview with Sean Ellis. If you want an intro to KISSmetrics, send me an email. I’ll put you in touch if there’s a fit. Thanks. – Nivi

Hiten Shah from KISSmetrics recently sat down with me to discuss how to optimize funnels with their upcoming analytics tool, KISSmetrics.

You may know Hiten from his Crazy Egg days and survey.io, which Hiten and I discussed in How to measure product/market fit with survey.io.

SlideShare: How to optimize your web apps with KISSmetrics
Audio: Interview with chapters (for iPod, iPhone, iTunes)
Audio: Interview without chapters (MP3, play anywhere)
Transcript: See below


You’ll get more out of this interview if you also read:

  1. Our interview with Sean Ellis parts 1 and 2.
  2. Our previous interview with Hiten: How to measure product/market fit with survey.io.


Here’s an outline and transcript of the interview. The interview and transcript are about 23 minutes long and we’ve highlighted some of the juicier bits for you.

  1. After fit, prepare for growth
  2. KISSmetrics helps you optimize your funnel
  3. KISSmetrics helps with all optimization steps
  4. First user experience isn’t necessarily the paid user experience
  5. KISSmetrics is most valuable after fit
  6. How Cloudfire uses KISSmetrics during fit
  7. Startups aren’t a science — but we’re getting closer
  8. How other people use KISSmetrics
  9. KISSmetrics is on it’s third iteration
  10. Why KISSmetrics’ hasn’t launched
  11. KISSmetrics tracks actions on a per-user basis
  12. KISSmetrics lets you calculate customer LTV
  13. Get more startup advice

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Thanks to FastIgnite, a startup advisory firm, for sponsoring Venture Hacks this week. This post is by Simeon Simeonov, the firm’s founder and CEO (and formerly a partner at Polaris Ventures). If you like it, check out Sim’s blog and tweets @simeons. – Nivi

The best strategy for not having to fire your co-founders is to not bring them on board in the first place.

One of the most common early-stage startup mistakes is building a weak founding teams. Since a good team is often the closest you can get to a good business plan, this one anti-pattern is the cause of many company failures. Before we dig into why this happens so frequently and what entrepreneurs can do about it, I want to share one of the formative stories from my early days as a VC.

An entrepreneur who should have fired his co-founders

Many years ago, I met a 20-something technical founder who had recently left graduate school with interesting technology in the enterprise search and knowledge management market. Beyond his compelling personality and the technology, he had an impressive approach that allowed him to deliver benefits to users without prior user setup or explicit user actions, using desktop and email client integration. To use a current analogy, it was like Xobni but better.

A week later, he came to Polaris with his founding team. He had three co-founders. They all had grey hair and so-so backgrounds. Over the course of an hour, I learned one of the three was a relative who, after hearing about the idea, pushed himself onto the team as “the business guy” and then promptly brought in a couple of former co-workers as co-founders. The net effect was that a backable founder had become essentially unfundable. I passed on the deal. As expected, the company went nowhere. I am friends with the founder and would like to back him some day.

This is an extreme example, but it underscores the randomness by which founding teams are created. Three disclaimers before we dive into the issues:

  • I’m not advocating that an entrepreneur goes it alone. Much has been written about the costs and benefits of partners when starting a company. I’m advocating for more thoughtfulness about the building of a founding team and more creativity around how to make progress with limited resources. See Venture Hacks’ post on How to pick a co-founder.
  • I’m not advocating that what’s best for the company in an abstract sense should trump personal relationships or commitments that have been made. I am advocating for greater care in making commitments and more openness around the balance between business and personal spheres.
  • I’m focusing specifically on founding teams here, but many of the lessons apply equally well to hiring in very early stage companies (before product/market fit has been proven).

How weak teams get built

Arrogance and ignorance, in small doses, are powerful tools that help entrepreneurs focus and execute against overwhelming odds. In larger doses they make a dangerous poison that kills startups. In most cases, they are the root cause behind weak founding teams.

It’s no secret that startup business plans tend to evolve over time, sometimes substantially. Yet, at any given point along that evolutionary path, many entrepreneurs are over-confident that, this time, the plan will succeed. Then they look at the founding team and, if they think they are missing a key role, they may bring a co-founder on board. This process repeats itself up to the point where either the company converges to what it will likely end up doing in the next few months or the founding team gets to a size that makes additions practically impossible.

I recently met an entrepreneur who started working on a consumer social media idea about a year ago. Thinking he was building a small dot-com, he brought on a college buddy who had done Amazon Web Services work as a chief technical officer (CTO). In a few months, the idea shifted toward working with agencies. He brought in a VP of marketing from the agency space, because he was confident that was where the opportunity was. After a few more months, the team realized there was only a services business in the agency space. Now they are pivoting towards expert identification/collaboration in enterprises, and neither his CTO nor his VPM is right for the team.

The entrepreneur in this example is a smart guy. But he didn’t have enough experience to understand what would be required for a co-founder role over the early evolutionary path of the company. He didn’t fully appreciate the opportunity cost of making these early hires given his limited recruiting network and the pre-product, pre-funding stage of the company. Further, he did not know how to evaluate a VP of marketing. He ended up with a communications-oriented exec who — beyond lacking understanding of the enterprise domain — is not very helpful in general with product marketing issues. This is how ignorance hurts.

What VCs think about bad co-founders

Keep in mind that when you recruit or you pitch investors, they don’t get the benefit of the history that might explain your decisions. Let’s imagine what goes on in a VC’s head:

“Shoot, this is a backable entrepreneur and the idea may have legs but the two other founders are B players and a poor fit for the company at this point. I could talk to the lead founder, but I don’t know about the personal relationships on the team and this can backfire. Also, I don’t want word getting out that I break founding teams. This can hurt my dealflow. Anyway, the CEO showed poor judgment in bringing these people on board. Also, there is still a lot of recruiting work to do whether the team changes happen before or after an investment. Frustrating… this could have been a good seed deal. Now it’s too complicated. I’ll pass using some polite non-reason.”

Agile founding teams

There is a principle in agile development that centers on minimizing wasted effort. One of the cornerstone strategies — supposedly one of Toyota’s rules, too — is to delay decisions until the last responsible moment. Because the future is uncertain, the idea is to make decisions with the most information. The emphasis is on “responsible,” because a lot of procrastination is bad too.

Last week, I wrote about how to raise money without lying to investors with this same principle. The logic also applies to building strong founding teams. Because you don’t know what your startup will end up doing, it can be a big mistake to hire the best people for this point in the company’s life.

The obvious solution is to build an amazing team of well-rounded, experienced athletes who can do anything that comes their way. The Good-to-Great companies put the right people on the bus and the wrong people off the bus. If you can do it, more power to you. However, you may have a few problems…

Entrepreneurs Anonymous

I am an entrepreneur, and I have team-building problems:

  • I am not exactly sure what my company will do.
  • I have limited resources and can’t have many people on my team.
  • My recruiting network is limited.
  • My company, especially pre-product and pre-funding, may not be very attractive.
  • I may not be the best person to evaluate people in _______ and _______.

Ten rules for building agile founding teams

Here are some specific strategies for building founding teams. There are no silver bullets. Some of the advice is contradictory and situation-specific. Caveat entrepreneur.

  1. Network, network, network. Learn how to learn through people. It’s the fastest way to understand a new domain. Value negative feedback. It often carries more information than a pat on the back. Expand your recruiting network, so you get access to better talent.
  2. Set clear expectations. When getting involved with someone, establish the right psychological contract from the beginning. Talk about what might happen if there is a pivot in an unexpected direction.
  3. Go easy on titles. Don’t give out big titles unless you have to and, even then, question why you have to. You can always “upgrade” someone’s title later if they perform well. They’ll appreciate it. On the flip side, big titles can cause many problems when you recruit or raise money.
  4. Structure agreements well. Founders should have vesting schedules with some up-front acceleration. In some cases, you can bestow founding status without giving founding equity with accelerated vesting.
  5. Be honest with and about your team. Get in the habit of discussing team fit with the business plan in an open, non-threatening manner. When you talk to experienced investors or advisors, be honest about the limitations of your team. Most likely they see any warts just as well or better than you, and you can only win by showing you have a firm grip on reality.
  6. Hire generalists early. Hire specialists later.
  7. Hire full-timers reluctantly. You can only have a few of them in the early days, whether they are co-founders or not. Be picky. Don’t fall for the chimera of “If only I hire a __________, then I can _________.” This may be true, but only if the person you hire is perceived to be good and does a good job. The perception of the quality of your team is as important as reality for recruiting and fundraising.
  8. Find experienced part-timers. Sometimes you can get a lot of value out of very experienced people even if they only spend a few hours, or a day, each week with you. The key is to do this over a period of time and build context. Over time, experienced part-time employees can help in the process of building the company. They can help make many decisions — for example, around team-building, financing and the business plan — as opposed to any one decision. This is how I work with startups through FastIgnite. Depending on the situation, I’m an active advisor or co-founder and/or acting CTO. Other people, like Andy Palmer, take on a board or acting CEO role.
  9. Find the right investors. Seek investors who pride themselves on their recruiting abilities and have a track record of helping startups build teams. These investors may see the holes in your team as an opportunity instead of a problem, as long as they feel confident the company is a good recruiting target. Some firms have internal recruiting teams led by experienced former executive recruiters. Examples include Benchmark (David Beirne) and Polaris (Peter Flint). Others, such as General Catalyst and Founders Fund, favor partners who are former entrepreneurs with deep networks and team-building experience.
  10. Fire your co-founders. If you are behind the 8-ball and see your team as a key constraint, you should do something about it. Don’t wait for an investor or someone else to do it for you. The non-CEO co-founders can fire their CEO co-founder, too (or change their role and level of responsibility). This happened at a social commerce startup in the Bay Area I liked. The CEO came up with the idea (kudos to him) but he had enterprise background and provided little value-add. His two co-founders were responsible for most of the progress. It took them too long to reshuffle things. By that point, they’d made a bad impression in front of too many investors. The team fell apart eventually.

If you successfully apply these strategies, you stand a better chance of going after the right people at the right time and bringing top talent on board.

You may not even have to fire your co-founders.

More: See Lee Jacobs’ posts on How to break up with your investor and How to break up with your co-founder.

Over the last few months, we’ve built and tested a new “ad” format on Venture Hacks that I really like. I’m writing this post to launch it (voila), describe the ads, and pitch new sponsors.

The ads

You’ve already seen the ads. They’re ‘sponsor posts’ like How to raise money without lying to investors by Simeon Simeonov. They’re labeled with an image like this,

and an introductory message from us: “Thanks to FastIgnite, a startup advisory firm, for sponsoring Venture Hacks this month…”

Why they rule

We expect sponsor posts to meet the same standards as our own posts: startup advice that tries not to suck. I think we’re succeeding. Sponsor posts get 50-150 retweets by cool people and 10-30 substantial comments. They get on the front page of Hacker News and Techmeme:

The sponsor posts often perform better than our own posts. They do well because you read them and spread the word. Thank you. And the sponsors are already great bloggers, so all we have to do is give them a little distribution bump.

Our challenge now is to maintain and increase the quality of our sponsor posts. Upcoming sponsors include George Zachary from Charles River Ventures and WordPress’ lawyer, Matt Bartus from Dorsey & Whitney.

For prospective sponsors

Sponsor posts are a great way to start a conversation with the Venture Hacks community — one of the best startup communities on the Web. They’re a chance for our readers to get inside the minds of their potential business partners — whether you’re a VC, lawyer, startup, or service provider. Past sponsors call it a “no-brainer.”

Sponsor posts get 5000+ views, 50-150 retweets, 10-30 substantial comments, and 50-100 new Twitter followers. We’re the only site in the world where the ads perform as well as the content. Learn more about sponsoring Venture Hacks.

Asking for your help

We want to ask for your help. Who should be sponsoring Venture Hacks? Who do you want to hear from? Who has a great blog that needs more distribution? Please send them a link to this page describing our sponsor posts and ask them to consider sponsoring Venture Hacks. And please send me your suggestions in the comments.

I recently described our sponsor posts to Eric Ries and he called them “ads that are really content you can share.” I like that a lot.

Thanks to FastIgnite, a startup advisory firm, for sponsoring Venture Hacks this month. This post is by Simeon Simeonov, the firm’s founder and CEO (and formerly a partner at Polaris Ventures). If you like it, check out Sim’s blog and tweets @simeons. – Nivi

“Prediction is very difficult, especially if it’s about the future.”

Niels Bohr, Nobel Prize winner

By penalizing entrepreneurs who are humble and honest about how their companies will grow, many investors cause entrepreneurs to over-promise (and later under-deliver) when they’re raising money.

The histories of some of the best-known technology companies demonstrate the power of luck, timing, the mistakes of incumbents, and solid execution.

Execution is the main tool under a startup’s control but it’s often under-valued by investors.

So it’s not surprising that most entrepreneurs come to pitch meetings armed with very precise statements about a very uncertain future and a list of proven strategies guaranteed to make their company successful. While sitting through these pitches, I sometimes wonder which is worse: the entrepreneurs who know they’re spinning tall tales or the ones who “got high on their own supply.”

VCs and entrepreneurs collaborate to lie about the future

Instead of bringing entrepreneurs back down to earth, some investors push them further into orbit. Some VCs ask a seed-stage, pre-product startup for a detailed five-year financial plan. When I was a partner at Polaris Ventures, I saw many of these spreadsheets built “for fundraising purposes.” We didn’t ask for these spreadsheets — entrepreneurs had usually built them after meeting other, less early-stage, investors.

I find the process of planning — and understanding how a founder thinks about a business — educational and valuable. But pushing the exercise to the point of assumptions layered upon assumptions is not just wasteful, but dangerous, because it sets the wrong expectations.

After a few pitches, entrepreneurs realize that the distant future is safer territory than the immediate. It’s easier to boast about 30 must-have features your product will have in three years, than to show the three must-have features in the current prototype. It’s easier to talk about how you’ll recruit world-class CXOs when you’re big and successful, than to show a detailed plan for bringing in an amazing inbound marketing specialist, when everyone on the team is getting paid below-market rates to conserve cash. The examples go on and on.

I’ve co-founded four companies. The two that most quickly and easily raised money did it with nothing but slide decks. Both were funded by Polaris, which has a lot of experience with very early stage investing. We didn’t waste time over-planning the future in those two companies.

And for good reason. Both startups ended up quite different than the fundraising presentations promised — for solid, market-based reasons that were invisible during diligence. Plinky acquired a new product line and became Thing Labs. 8th Ring failed quickly and cheaply, only seven months after funding. The CEO and I decided the execution risk was too high. And, in retrospect, we were right: our only competitor had an unexciting exit a few years later.

Over-promising causes startups to throw away money

Over-promising is not a problem when it comes with over-delivery. But the overwhelming majority of startups fail to meet the promises they’ve made during fundraising. After years of observing this pattern, I’ve come to believe that over-promising can actually cause under-delivery. Entrepreneurs over-promise to raise money easily and set themselves up for pain down the road.

How? The reasons have to do with information signals, expectation setting, and the psychological contracts between entrepreneurs and investors. It’s very hard to pitch one story today and then change it the day the money hits the bank, especially if you’ve drunk the Kool-Aid.

An overly rosy pitch leads to expectations and fateful commitments that downplay the variability of the future. Decisions are made based on assumptions rather than tested hypotheses. The burn goes up earlier. The sales team is hired much too soon. In venture funds, over-promising also spreads from the investing partner to the rest of the partnership. It can also spread from the company to its customers and partners, further extending the reality distortion field.

If you’re Apple and you’ve got Steve, that’s awesome. For everyone else, it can get rough. I saw this play out with one of my companies that was expanding internationally (the reason why the company had raised money). The world was going to be our oyster and, before the reality that our go-to-market strategy wasn’t as effective as everyone had hoped set in, we had burned through a good chunk of capital.

Find investors you don’t have to lie to

How should you choose between being honest (and hearing “no” a lot) vs. amping up the pitch and risking the anti-patterns above? I give two answers to the CEOs I work with at my startup advisory firm FastIgnite.

First, I strongly advise startups to go to venture firms where the decision process is more collaborative and less “salesy.” One of the main reasons a VC will push an entrepreneur to over-promise is his need to sell a deal internally.

Second, pitch investors with a track record of valuing a team’s ability to execute, over any specific strategy or execution plan. While most firms pay lip service to this cliché, few do many investments this way. Here are some examples from my experience in the past few months:

  • On the smaller side, Betaworks and First Round Capital get this. Their portfolios and their philosophy show it. I look forward to working with them some day.
  • Among VCs, General Catalyst has repeatedly backed companies like Brightcove, m-Qube, and Visible Measures very early — with the understanding that many important questions will have answers only after months of execution. I’m actively partnering with them at FastIgnite.
  • Surprisingly, at the very high end, a private equity firm like Warburg Pincus can be a great place for the right early-stage entrepreneur. Last year, a Warburg entrepreneur-in-residence incubated Better Advertising, a company where I’m a co-founder and acting CTO. Better Advertising’s market and business model required a backer with staying power that exceeds most other investors’.

The firms above practice a form of agile investing by (1) not forcing entrepreneurs to over-plan for an uncertain future and (2) following the principle of minimizing wasted effort. Ultimately, it’s the investors’ responsibility to reward honesty with trust and cash. And I think that’s a win-win. I’m looking forward to discussing this with you in the comments.

If you like this post, check out Sim’s blog and his tweets @simeons. And contact me if you’re interested in supporting Venture Hacks. Thanks. – Nivi

Thanks to Walker Corporate Law Group, a boutique law firm specializing in the representation of entrepreneurs, for supporting Venture Hacks this month. This post is by Scott Edward Walker, the firm’s founder and CEO. If you like it, check out Scott’s blog and tweets @ScottEdWalker. He’s also writing a new series on VentureBeat: Ask the attorney. – Nivi

Last week I offered 5 New Year’s resolutions for closing deals in 2010. This week, I thought I’d have a little fun and address the issue of entrepreneurs’ frustration with lawyers. A recent tweet from Bram Cohen, the inventor of BitTorrent, captures this frustration well: “Lawyers are like phone companies. Their bread and butter is in tricking you into racking up minutes.”

There’s a time in just about every entrepreneur’s career when he or she has wanted, in the words of Shakespeare, to “kill all the lawyers”. In the spirit of David Letterman, here are my Top 10 reasons entrepreneurs hate lawyers (I should point out that “hate” is too strong a word to describe the feelings of most entrepreneurs, but it makes for a catchier title than “dislike” or “complain about”). Click here for a brief video version of this post.

#10 – “Because they don’t communicate clearly or concisely”

Lawyers love speaking legalese and hearing themselves talk. I learned this first-hand as a corporate associate for nearly eight years at two large New York City firms. The tax lawyers, the employee benefits lawyers, the antitrust lawyers and the rest all spoke their own language. As a corporate associate in charge of quarterbacking transactions, I dealt with the various legal specialists and had to learn their mumbo jumbo. At times, I was as frustrated as the clients.

In the book Garner on Language and Writing, Former U.S. Solicitor General Theodore Olsen wrote,Legalese is jargon. All professions have it. All professions use it as a substitute for thinking, and they all use it in a way that makes them appear to be superior. Actually, they appear to be buffoons for using it. The legal profession may be the worst of all professions in using jargon. It’s not necessary to communicate that way. You’re really not communicating, and you’re not really thinking.”

#9 – “Because they don’t keep me informed”

Lawyers often keep their clients in the dark. The real estate lawyer I hired to handle the sale of a property came highly recommended and seemed like a good guy. But I never knew what was happening throughout the process. I showed up to the scheduled closing only to learn it was postponed because of some wrinkles, including the buyer’s financing.

Tom Kane, a legal consultant, notes: “[A] failure to communicate often (as in constantly, frequently, persistently, regularly…) is not only foolish from a professional standpoint (as in discipline by the bar, keeping professional insurance premiums reasonable, and so forth), BUT it is just dumb marketing. One could even say it is marketing malpractice.”

#8 – “Because they are constantly over-lawyering”

Corporate lawyers often have a one-size-fits-all approach to deals. I recently represented a software company in a relatively small business sale (about $10 million). The buyer was represented by a large law firm that sent an acquisition agreement with three pages of environmental representations. When I explained that none of the environmental reps (or indemnities) was applicable to the target because it was a software company with one office lease, the corporate counsel got on a soapbox about his client “not assuming any environmental risks.” He even patched in the firm’s environmental lawyer to support his argument.

As John Derrick, a California appeals specialist, points out in his book Boo to Billable Hours, “Just as the cost-plus contractor has no financial incentive to keep the price down once hired for the job, so the lawyer who charges by the hour has little incentive — at least in the short term — to keep down the hours billed. To the contrary, the lawyer’s incentive is to bill as much as possible. The result can be unnecessary lawyering.”

#7 – “Because they have poor listening skills”

While lawyers love hearing themselves talk, they are often not very good at listening. Entrepreneurs want their lawyers to listen carefully to their concerns and address them appropriately; and they don’t want to be interrupted. I feel the same way, particularly when I am negotiating a transaction and trying to close a deal. I have sat in too many conference rooms negotiating with other lawyers as they played with their Blackberries and answered calls on their cell phones. This is not only rude, but it’s also bad lawyering.

From the Wabet Blog: “While great corporate lawyers have several different attributes, one stands apart from the rest: being an exceptional listener. First of all, it’s essential that the corporate lawyer is always ready and able to listen to the client’s description of [his or her] goals and needs. This sounds trite, but involves a set of skills that is more than simply hearing the words spoken or reading the words on the written page. The exceptional corporate lawyer looks beyond the words to delve into the facts, circumstances and other aspects that define the situation… Some of the skill is derived from training, but to a large extent the exceptional corporate lawyer applies his or her experience and the wisdom derived from that experience.”

#6 – “Because inexperienced lawyers are doing most of the work”

This is the dirty little secret at most law firms, particularly large ones. It even has a name: “leverage”. Law firms try to create the highest possible ratio of associates to partners. The higher the ratio, the more money the partners make. For most entrepreneurs, this generally means paying for the training of young associates.

I discuss this issue in my blog post Behind the Big Law-Firm Curtain: The Good, The Bad, The Ugly, “The reality is that the smaller the client — the smaller the transaction — the further down the ladder the work gets pushed at the big law firms. That’s the way these firms work. The entrepreneur may meet the senior partner at the first meeting for his $15 million acquisition or $3 million financing, but that partner then goes back to his office, calls the assigning partner and gets some young associate to start cranking out the work.”

#5 – “Because they spend too much time on insignificant issues”

Lawyers are notorious for failing to prioritize issues. This is especially true in small transactions. Since I moved to Los Angeles from New York City in 2005, I have handled predominately middle-market M&A transactions, financings and restructurings, a departure from the billion-dollar deals I handled in New York. I expected lawyers on these transactions to produce documents relatively quickly and focus on the key issues of a deal, particularly in venture capital transactions that benefit from standardized documents from the National Venture Capital Association. Instead, I found much of what I found in New York: lawyers spending needless time fighting over insignificant issues.

Foundry Group co-founder and managing director Jason Mendelson recently asked, “Why can’t lawyers know when to leave well enough alone and not feel like every piece of paper needs a mark up? Especially given how expensive lawyers are these days, why on earth would the culture of ‘must mark up documents to show value’ persist? (Answer: lawyers make more money). Especially in the world of venture financing, this is very frustrating.”

#4 – “Because they don’t genuinely care about me or my matter”

Too few lawyers are passionate about the practice of law. Before launching my own firm, I worked alongside many big-firm lawyers who didn’t seem to enjoy what they were doing. This translates to indifference toward clients.

This quote from Zappos CEO Tony Hsieh in a recent New York Times interview struck a chord with me: “I just didn’t look forward to going to the office. The passion and excitement were no longer there. That’s kind of a weird feeling for me because this was a company I co-founded, and if I was feeling that way, how must the other employees feel? That’s actually why we ended up selling the company.”

That’s how I felt at the law firms where I worked. There were a number of passionate superstars at each of my previous firms. But many others were burned out and just going through the motions. “Just another fuck’n deal,” one of my former colleagues once complained to me. That’s why I launched my own firm: to create a team of passionate, hard-working corporate lawyers who love what they do and love helping entrepreneurs.

#3 – “Because their fees are through the roof”

As I discuss in the introductory video on the home page of our website, the traditional law firm business model is broken. Legal fees have sky-rocketed over the past decade, with lawyers at some national firms billing more than $1,000 per hour and lawyers at smaller, so-called “regional” firms, billing more than $600 per hour (see “Law Firm Fees Defy Gravity, Annual Survey Shows”). The number one thing driving these outrageous rates: overhead. Traditional law firms simply pass huge overhead costs onto their clients — expensive office space with lavish artwork and dramatic views; large support staffs complete with librarians, and receptionists; and, of course, high-paid associates.

As a result of the recession and this broken business model, large law firms have recently shed associates in large numbers. LawShucks reports, “2009 will go down as the worst year ever for law-firm layoffs. More people were laid off by more firms than had been reported for all previous years combined.” But as Dan Slater argues in his recent New York Times DealBook post, Another View: In Praise of Law Firm Layoffs, “These layoffs — which in many cases have been paired with salary freezes or cuts and significant reductions in law school recruiting –­ are the best thing to happen to the legal industry in years. Call it a blessing amid recession. Start with the benefit to cost-conscious corporate counsel, who for too long have been bilked by a law firm compensation model that leads lawyers to prioritize their ‘hourly quotas,’ which determine year-end bonuses, over quality service.”

#2 – “Because they are unresponsive”

We’re all busy, but that’s not a viable excuse for failing to promptly return a client’s phone call or email. Clients may have differing definitions of “promptly,” but one business day is a good starting point. I experienced unresponsive lawyers as a client in personal matters, and I experience it as a corporate lawyer trying to close deals on behalf of my clients. Entrepreneurs crave immediacy (and so do I).

A recent deal I was on ran days late, requiring an all-hands conference call to finalize a few key issues in the acquisition agreement. I distributed an updated version the same day with instructions to the lawyer on the other side to call me for an update before he left for the weekend. The weekend passed. I heard back from the lawyer on Monday afternoon, over email — and he had sent a new blacklined version with all new issues raised.

#1 – “Because they are deal-killers”

Lawyers are often viewed as deal-killers because of their failure to set a positive tone and their annoying habit of raising all sorts of reasons why a particular deal won’t close or why a particular idea won’t work. One of the better lawyers I worked with at a firm often said: “Good lawyers are able to identify significant potential legal problems; great lawyers provide solutions to those problems.”

As James Freund, a professor and retired partner at Skadden Arps in New York, points out, “In a transactional practice, nothing comes easy. There are invariably two opposing points of view on significant issues, and the parties will even clash… over a circumstance that may never come to pass. Every disputed issue has to be resolved in order for the deal to take place. And the business lawyers bear the primary responsibility for getting it done. Viewed in its broader context, this activity falls under the rubric of problem solving. Unless you’re a problem solver, you’re unlikely to be an effective business lawyer. And the problems that stand in your way aren’t limited to transactional matters… they can involve dealings with regulatory agencies, tax planning, strategizing about how to protect intellectual property, and on and on.”


While much of this list includes criticisms of my industry, I hope it helps initiate dialogue among entrepreneurs and the lawyers who represent them, to improve the value of the services we offer. And, please remember, I put this list together in the spirit of having a little fun. What experiences have you had with lawyers? Feel free to share in the comments section.

If you like this post, check out Scott’s blog and tweets @ScottEdWalker. He’s also writing a new series on VentureBeat: Ask the attorney. If you want an intro to Scott, send me an email. I’ll put you in touch if there’s a fit. Finally, contact me if you’re interested in supporting Venture Hacks. Thanks. – Nivi

Thanks to Walker Corporate Law Group, a boutique law firm specializing in the representation of entrepreneurs, for supporting Venture Hacks this month. This post is by Scott Edward Walker, the firm’s founder and CEO. If you like it, check out Scott’s blog and tweets @ScottEdWalker. – Nivi

It’s a new year — which means it’s time to make resolutions. Rather than write about my resolutions, I decided to put on my lawyer hat and advise entrepreneurs on what I think their New Year’s resolutions should be. During my 15-year career as a corporate lawyer (including nearly eight years at two major law firms in New York City), I have seen entrepreneurs make certain fundamental mistakes over and over again. So what better way to welcome in the new decade than to recommend the following resolutions to entrepreneurs…

Resolution 1: “I will create a competitive environment when I’m doing deals”

There is nothing that will give an entrepreneur more leverage in a negotiation than a competitive environment (or the perception of one). Every investment banker worth his salt understands this simple proposition. Not only does competition validate a firm’s interest, but also it appeals to the human nature of the individuals involved. Competitors can be played off each other and, as a result, the entrepreneur will be able to strike the best possible deal.

I learned this important lesson as a young corporate associate in New York City. As I discuss in my video post, Lessons Learned in the Trenches of Two Big NYC Law Firms, I recall having two M&A transactions on my plate: one was a divestiture — i.e., the sale of a division of a multinational corporation being auctioned by an investment bank; and the other was the sale of a private company to a competitor (with no i-bankers involved). In both deals, my firm was representing the sellers but, as we worked our way through the negotiation process of each deal, we ended-up with two completely different acquisition agreements with respect to the material terms.

In the auctioned deal, because the i-banker was able to play the prospective buyers off each other and create a competitive environment, the final agreement was extremely seller friendly and included broad materiality qualifications, a huge basket/deductible and a cap on seller’s liability of 10% of the purchase price. In the private-company transaction, however, there was only one prospective buyer — and the buyer’s principals knew that the seller was anxious to sell and thus were playing hardball. The deal terms ended-up being extremely buyer-friendly and included a large portion of the purchase price being escrowed and a cap on the seller’s liability equal to 100% of the purchase price.

The lesson learned is that you must create a competitive environment (or the perception of one) in order to have strong negotiating leverage. There is, however, one important caveat that entrepreneurs should keep in mind: this game must be played carefully and is better handled by someone with experience. The last thing an entrepreneur wants is to end up with is no deal at all.

Resolution 2: “I will leave my heart at home”

You have to think with your head, not with your heart — particularly when you’re doing deals. The best deal guys are masters at taking their emotions out of transactions and being extremely disciplined. They will just walk from a deal if they get out of their comfort zone (e.g., with respect to the price, risk profile, etc.), regardless of how much time and money they have spent.

On the other hand, most entrepreneurs become emotionally wedded to a particular transaction and are unable to maintain their objectivity as they move further along the deal process. They get all excited as soon as someone waves some money at them and allow themselves to get drawn into the money guy’s web. It is critical that entrepreneurs understand this dynamic. Entrepreneurs will generally be negotiating with guys on the other side of the table who are far more deal savvy than they are – venture capitalists, private equity guys, etc. – guys who are masters at playing on their emotions.

This is why it is so important for entrepreneurs to establish a game plan (i.e., dealbreakers) before the negotiating process begins and to have the discipline to stick to the plan and be willing to walk, if necessary. If an entrepreneur is seeking venture capital financing, he should sit down with his transaction team before reaching out to the VC’s to establish his dealbreakers with respect to key terms, such as valuation, the liquidation preference, board composition, etc. The same approach should be followed if he’s interested in selling his company: What’s the lowest purchase price you’ll accept? What’s the highest cap on liability you’ll agree to? Will you agree to escrow part of the purchase price? If so, how much and for how long? Once you establish the dealbreakers early on, you can take your heart out of the equation and think with your head.

Resolution 3: “I will work my balls off”

This is the advice a senior partner gave me when I was a young corporate associate at a major New York City law firm: “If you want to be a great lawyer, you have to work your balls off and make practicing the law the number one priority in your life.” He explained that this means everything else in your life has to be pushed aside, and you need to “work, work, work.” And when you’re not working, he added, you need to be reading treatises and articles discussing the deals you’re working on to get a deeper understanding of the significant issues. When I explained to him that, after three months, I had been working nearly every weekend and that my girlfriend was ready to leave me, he told me that I need to get a new girlfriend.

I received similar advice from Harry Hopman, my old tennis coach (and the winningest coach in Davis Cup history), when I was playing tennis in the minor leagues after college. He preached to me that: “It all comes down to one word — desire. How badly do you want it? How much are you willing to sacrifice?” And he was right. When I was traveling and playing tournaments in Europe and South America, I noticed that the best tennis players were generally the hardest working; the qualifiers were the ones going out drinking every night, not the top seeds. Sure there were exceptions — like John McEnroe — but the exceptions were rare.

I have seen this same pattern during my legal career: the most successful clients tend to be the hardest working. The private equity guys and hedge fund guys I represented in New York City were animals; working around the clock and cranking out deal after deal. I attribute a lot of their success to just plain hard work. In 2005, I moved out here to California to help entrepreneurs, and it’s been a mixed bag in terms of the work habits that I’ve seen. Some of my clients are intense and put in the long hours; others, however, are just dreamers — and they are the ones who struggle. In short, there are no shortcuts to success.

Resolution 4: “I will not let my investors screw me”

Here’s the advice I give all my clients to avoid getting screwed by their investors: do your due diligence prior to accepting any money. The number one mistake I have seen entrepreneurs make in any deal is the failure to investigate the guys on the other side of the table. Remember, you will, in effect, be married to your investors for a number of years. Accordingly, entrepreneurs must do what any bride or groom does prior to tying the knot — date for a while and, of course, meet the family.

What does this mean in practical terms? It means surfing the web and learning everything you can about the particular firm making the investment and, more importantly, the particular individuals with whom you are dealing (and who, presumably, will be sitting on your board for a number of years); it means breaking bread and having a couple of beers with the potential investors; and it means getting references and talking to other entrepreneurs and founders who have done deals with them. Issues to address include: How have they treated their other portfolio companies? Are they good guys or jerks? Can they be counted-on and trusted? Do they share your vision for the venture? Will they add significant value (e.g., through contacts, domain expertise, etc.)?

There is an outstanding video discussion on Mixergy.com between Brandon Watson, a smart entrepreneur (currently at Microsoft), and Andrew Warner, the founder of Mixergy, as to what could happen if you don’t adequately diligence your investors. Brandon is extremely candid and discusses how he got “bullied” by his board. Moreover, he expressly notes in the comments to that post that, “the diligence factor was that I knew them, but had never taken money from them. It’s hard to know how people are going to react when they are at risk of losing money because of something you are directly responsible for until you are actually at that point.”

Resolution 5: “I will retain a strong, experienced lawyer to watch my back”

This is obviously a bit self-serving, but every entrepreneur needs a strong, experienced lawyer to watch his back. There is just too much at stake for entrepreneurs to be (1) using sites like LegalZoom, (2) pulling forms off the web and trying to play lawyer, or (3) retaining the cheapest lawyer to save money. And as the Madoff affair and other recent high-profile cases demonstrate, there are a lot of unscrupulous characters out there trying to take advantage of unsophisticated entrepreneurs.

There are also more subtle potential problems entrepreneurs need to be protected from, including the inherent conflict of interest that certain service providers have. For example, entrepreneurs need to be careful with investment bankers, who generally only get paid if a particular deal closes. Indeed, a middle-market i-banker’s entire year can be made or broken based on whether or not he can close one or two deals.

Unfortunately, I experienced this issue first-hand shortly after moving to California when I got pulled onto an M&A deal in which an i-banker stuck his finger in my chest and warned, “We’re going to get this deal done despite you fucking lawyers.” He then later complained to the managing partner (who had the client relationship) that I was blowing up the deal because I had retained special environmental counsel from my old NYC law firm and we were pushing too hard on the environmental indemnity. Good work by the i-banker (and cheers to my former managing partner) for getting the deal closed by watering down the environmental indemnity: less than six months later our client’s company was indicted for environmental problems that it inherited as part of the acquisition.

The bottom line is that a strong, experienced corporate lawyer will sober the entrepreneur and lay out all of the significant legal risks in a particular transaction; he will then push hard to negotiate reasonable protections. If the deal sours and lawsuits are filed, well-drafted documents with appropriate protections become a kind of insurance policy to the entrepreneur.

If you like this post, check out Scott’s blog and tweets @ScottEdWalker. If you want an intro to Scott, send me an email. I’ll put you in touch if there’s a fit. Finally, contact me if you’re interested in supporting Venture Hacks. Thanks. – Nivi

Thanks to Atlas Venture for supporting Venture Hacks this month. This post is by Fred Destin, one of Atlas’ general partners. If you like it, check out Fred’s blog and tweets @fdestin. – Nivi

In Part 1 of The Arrogant VC, I discussed 4 reasons why VCs are disliked by entrepreneurs:

  1. Poor first impressions
  2. Getting strung along or left at the altar
  3. Getting a raw deal
  4. Great (but misguided) Expectations

This post contains 4 more reasons why VCs are disliked by entrepreneurs. Both of these posts contain direct quotes from entrepreneurs with real, hands-on experience with (often prominent) VC’s, sometimes through multiple companies and fundraising.

5. Unwanted advice, poor communication, and lack of operational sense

“While VCs are always happy to dish out advice, this feels disingenuous from people who have never actually built a company or had a knockout success as an investor. Learning from mistakes is far less useful than emulating success.” One entrepreneur goes further in accusing VC’s of seeing everything through the lens of money: “Often times they have zero operational experience (how to launch a company/product or manage customers), don’t understand marketing beyond just building their own brand, and see money as their ticket for everything.”

VC’s are often ex-lawyers or bankers and some have a tendency to feel safe with “experienced suits” that sometimes do nothing but drive the burn rate up and compound cash-flows problems. Entrepreneurs are often “driven, creative types who want out of larger organizations,” whose traits map poorly to those of many VC’s. Ultimately, since many of them don’t understand the businesses deeply, they “try to make up [for] this particular information asymmetry with legal enforcement.”

Some VC’s are not that shy about it. One partner in a tier I fund described his role in this way: “Industry experience is not that important. I see my role on a board as to challenge every decision the management makes.” Here’s a variant on the same theme: “I don’t give a s**t about the company’s strategy, my job is to come here once a month and check what you are doing with my money.” QED.

6. Different objectives and time frames

“It takes patience and time to build a great business, and target returns and time frames (e.g. five times in five years) can get in the way. On the other side, entrepreneurs burn out and blow up all the time, so it’s tough to keep both sides aligned and together for a long time.”

Sigurd says “short investor time frames to meaningful exits means forcing businesses to scale too much and too fast (and offsetting this risk through a portfolio approach), whereas the entrepreneur must offset the market and product risk by slower movement and something akin to agile development.” David agrees on this natural misalignment of interests: “VCs need home runs, and entrepreneurs need singles at least on their first couple of companies.”

The going really gets tough when entrepreneurs lose their original sponsor. “The new guy is either too junior, does not know the business, or feels he has the right to wash his hands of the mess left by his departing partner.”

7. Arrogance and lack of empathy

At the end of the day, most entrepreneurs completely understand that objectives are not always aligned and that VC’s work for funds that need to return capital. What they have trouble with regardless, are “double standards“. One entrepreneur who has raised money multiple times says, “A lot of VCs do things no regular employee would dare to do but are largely unaccountable for those behaviors: forgetting about board meetings, showing up 20 minutes late, bullying the team or CEO, being generally unavailable, paying no attention in meetings because they are arranging a golf game on their BlackBerry, failing to read the board pack before the meeting, so the actual meeting is remedial in nature.” the message seems to be, “Don’t treat me the way I see fit to treat you.”

Net-net, VC’s are too often “out of touch with the reality of entrepreneurs.” “They are often times elitist, clashing with the very scrapiness of their entrepreneurs.” Arrogance is the word. “I was told forcefully ‘you will fail’ and that I should join another startup… funded by the very same VC.” “I spent 4 years in poverty ignoring my family and my friends to get the company to this point, and now they want me to vest my shares.” Yet another: “I have mortgaged my house, I have spent all my money, my family lives on pizza coupons and now you are telling me you want customers and a live product to boot? Why don’t I call you back when I have gone public, bozo. You call yourself a risk taker? You want 30% of my company when all the risk has been taken out?” (I added the pizza coupon piece for effect, but you get the idea).

Finally, entrepreneurs feel VC’s are “crap at sharing the wealth,” recognizing “how tough it is to create value” or “properly re-incentivising managers who gave up many years of their lives, effectively abusing a position of power and often manipulating entrepreneurs by threatening their reputation.”

Bottom line: “VC’s really don’t take any personal risk but expect everyone else to…”

Add to this some “dumb practices” such as demanding board remuneration and monitoring fees or “submitting ridiculous expenses” to complete a picture that betrays a complete lack of empathy.

8. Dark Side of the Force

Finally, some ugly business behaviour. A fairly common practice seems to be what you might call “slow strangulation”, whether by design or not. “An equity investor will knowingly under-capitalize your startup only to gain control of it once the opportunity manifests itself by use of a wash-out round; milestone financing and abusive board control are used for similar tactics. As a consequence, myself and others now prefer to bootstrap/self-fund rather than taking any amount of early-stage capital that will not *clearly* take the company to the next level.”

This is a common gripe with smaller funds, who have badly under-performing portfolios and little follow-on reserves, and who fall back on such slow strangulation of businesses they fund by trickling money, gradually washing every one else out, and hoping that 50% ownership for little money invested will somehow pay back for the rest of their portfolio. Smaller regional, government-backed funds get a particularly bad rep in this area. Lacking experience and confidence, they rely on punishing paperwork and self-anointed gurus to help them through the hard process of building successful companies.

Entrepreneurs have come forth with other dubious practices, including outright lying about the state of the business when refinancing, disclosing confidential information or personal confidences, negotiating on behalf of management and forcing deals through, making a mockery of governance rules. One systemic problem appears to be a failure to represent the interests of the company in board meetings, but rather short-term investor interests. “This is a plague on the industry and makes the board worse than useless to the company.”

Another entrepreneur identifies what he calls “classic VC tricks” such as “firing the team just before an acquisition, term sheet bombs, hiding or obscuring key information, manipulating the team to try to change ownership or board composition, changing deal terms just before closing.” He adds: “These destroy alignment and trust, and without some alignment and trust the necessary working relationship and motivation is destroyed.”

The worst I got related to VC’s pushing to recover shares from the heirs of a deceased co-founder under a reverse vesting provision. As the contributor put it, “it will take a lot of good karma from a lot of VC’s to make up for this one.” I was stunned.


Last words to entrepreneurs from Rory Bernard: “Choose your VC’s with care. Good ones transform your business, bad ones wreck it.”

And to VC’s: “tread softly, remember that in a position of power, you can do many sensible things but a few stupid ones and end up with a ‘George Bush’ problem, and as a result the approval rating of Dubya.”

If you like this post, check out Fred’s blog and his tweets @fdestin. If you want an intro to Atlas, send me an email. I’ll put you in touch if there’s a fit. Finally, contact me if you’re interested in supporting Venture Hacks. Thanks. – Nivi

Thanks to Atlas Venture for supporting Venture Hacks this month. This post is by Fred Destin, one of Atlas’ general partners. If you like it, check out Fred’s blog and tweets @fdestin. I’ve also generated an MP3 version of this post. Let me know if it’s useful. – Nivi

Below is the summary of all the answers I received to my recent post, “Tell me why VCs are disliked by entrepreneurs”. There is a shorter and easier to stomach version on Xconomy if you prefer, here. I have tried to keep my role as editor limited to re-organising, so this remains true to the commentary. I would add that most or all of these entrepreneurs had real, hands-on experience with (often prominent) VC’s, sometimes through multiple companies and fundraising. And yes, I also plan on writing a feature about the “good side” soon…

The VC-Entrepeneur relationship seems damaged. Whilst business partnerships gone bad and company failure can lead to fallout, this is different. I wanted to find out why and used my blog to ping the entrepreneur community to try and understand this better, listen to my audience as it were, and share the feedback.

As with all articles of this kind, it is plagued by generalizations and simplifications. In trying to do justice to the sixty detailed and mostly confidential responses that I got, I probably lost some of the color and detail. But for anyone interested in rebuilding the social contract with entrepreneurs and getting our VC mojo back, the scale of the problem should be apparent.

Clearly as VC’s our job is not be loved but to contribute in building great business and return money to our shareholders. Read on regardless; as you will see, the status quo is not an option.

A common answer I got was “sour grapes”. As Richard Jordan put it, “failures breeds frustration” and there is a natural tendency to spray the blame around. Externalize guilt as resentment, combine it with some old fashioned finger pointing, and there you go.” Many VC’s excel at that too. Sometimes anger stems from the “sheer exhaustion from being told ‘no’ too many times”. Now let’s dig deeper.

Poor first impressions

Richard Jordan (read him) says: “probably more than half of the VC pitches I have done have involved participants on the VC side who have behaved in a rude and disrespectful manner“. Arriving late, cutting out early, reading their blackberry, constantly interrupting pitches, taking calls, you name it. Some of the pitching experiences border on the ridiculous, as evidenced by a young founder who got invited to pitch for fifteen (yes, fifteen) minutes with five minutes Q&A, only to find the meeting started ten minutes late and was not to be extended…

The absence of feedback loop is a common theme with entrepreneurs griping about “dozens of unanswered calls and mails, from people they met. If nothing else works, what are your PA’s for?” Another common gripe is the need to be dealing with an Associate who needs to sell his deal internally and is often insecure and not clear himself on his chances of getting the deal done.

Even in early meetings, the lack of “empathy with and experience of the startup and the sacrifices involved” can leave entrepreneurs fuming. Finally, many entrepreneurs complain about a lack of confidentiality with their pitches sometimes “landing on competitors’ desks days after the meeting”. In a recent example, a well known General Partner interrupts 50 minutes of cross questioning with this casual statement, “By the way, I am personally invested in a new startup that is targeting this segment”.

Getting strung along or left at the altar

“Raising capital depletes far more energy than investors realize”, says one entrepreneur. “Getting a ‘no’ is actually fine from an entrepreneur point of view (one has to be rejection-proof anyway), but to preserve their opportunities many VC’s tend to string along entrepreneurs forever, blatantly lying about deal status only to let it fall apart at the last minute, wasting an entrepreneur’s time and energy.”

Many investors appear to be “vague on their decision and engagement process, which tends to be liquid.” Some VC’s promise term-sheets that never come, others withdraw at closing (the worst I personally heard was an SMS turndown by a “tier one” VC followed by a competitive investment), others still don’t bother checking conflicts of interest. “VCs are too opportunistic in their behaviour,” says one experienced entrepreneur.

A common gripe concerns the lack of clarity (or absence) in the rules of the game. Some companies are forced to jump through endless hoops to get a tiny round done whilst others raise a ton of money at seed with no substance. VC’s pretend to do seed but then say no to everything that is early and want revenues, customers, a business model, and a team. Entrepreneurs are confused and sometimes angry about this, as they feel fundraising is like a marathon with no end, when the hills keep getting steeper along the course. “The whole process leaves me with this feeling that landing funding is nothing more than getting lucky with the right pitch on the right day with the right person in the room,” says D. It makes you feel like “a sort of magic and certain incantations and artistry is required,” yet despite that, “investors often still fail to ask the right questions, the hard questions”.

Getting a raw deal

“Taking capital does feel a bit like making a deal with the devil after all.” Entrepreneurs fundamentally want to change the world and dealing with the Money Men is often a compromise they would rather do without.

“The entrepreneur is a bit like a child who’s just learned the rules of chess — he’s studying the current move intently, but he’s rarely thinking far ahead. The VC is an old hand at this game — he knows its patterns intimately and can see how it’ll develop far into the future. The entrepreneur tries to play well, but the terms he fights for often turn out not to be important, while the terms he thinks are innocuous can surprise him in unexpected ways. Unless things at the company go astoundingly well, the entrepreneur comes away feeling like he was played — taken advantage of by someone far, far more experienced at this particular game.” Clauses like participative liquidation preferences, anti-dilution, aggressive reverse vesting, board control or simply shareholders’ rights come up frequently, with good reason.

“My own VC’s have been great. That said — like many entrepreneurs, I’ve only realized some of the longer-term implications of the documents I’ve signed well after the fact. This was enough to make me wary.”

Great (but misguided) Expectations

“Many entrepreneurs want an investor to fund the idea (equivalent to a TV production house looking for funds from a commissioning editor to make a show, and generate a profit from it). It often takes them a long time to realize that such VCs don’t exist. By which time they are bitter and tired and blame the VCs, rather than their own lack of understanding” of what it takes to get VC funding.

David Smuts believes there are two kinds of VC’s: “Careerists VC’s” and “Entrepreneur VC’s” and two kinds of Entrepreneurs: “Real Entrepreneurs” and “Wannabe Entrepreneurs”. “Entrepreneur VC’s behave in the best interests of the business they are investing in,” whereas “Careerist VC’s put their own career prospects first.” “Wannabe Entrepreneurs either hate all VC’s because they reject their business idea,” or “suck up to all VCs because they want their money.” Long story short: The goal is to match Real Entrepreneurs with Entrepreneur VC’s.

Continued in Part 2 with unwanted advice, arrogance, and the dark side of the force… (I’ve also generated an MP3 version of this post. Is it useful?)

If you like this post, check out Fred’s blog and his tweets @fdestin. If you want an intro to Atlas, send me an email. I’ll put you in touch if there’s a fit. Finally, contact me if you’re interested in supporting Venture Hacks. Thanks. – Nivi

Thanks to Atlas Venture for supporting Venture Hacks this month. This post is by Fred Destin, one of Atlas’ general partners. If you like it, check out Fred’s blog and tweets @fdestin. And if you want an intro to Atlas, send me an email. I’ll put you in touch if there’s a fit. Thanks. – Nivi

There is a behavior I witness in some first-time CEOs that I meet, not necessarily the younger and more mavericky generation, that I do not think is necessary, nor helpful. It’s an insidious but frequent tendency to let the board decide, rather than advise or approve. It goes like this…

Because VCs have blocking rights on some important decisions (approving the budget, your compensation, raising money), they are often able to wield way more power than their 20% ownership would suggest they should have. As a result, entrepreneurs often talk of coming to the board with their slides in hand, asking “what does the board want me to do?”, which is code-speak for, “I am here to ask for permission from my investors to do what I need to do.”

Entrepreneurs will present the strategy they believe in, but essentially allow the board (read: the investors) to walk straight through the carefully thought-out action plan and redesign the entire strategy in one swell meeting. The investor probably walks away feeling like he provided value and the entrepreneur now goes back to his team to explain that his investors puked over the team’s strategy and that the priorities have changed.

It’s the CEO’s fault

That may be the product of investor behavior, but I would argue this is the CEO’s fault. Nature abhors a leadership vacuum, and VCs will fill that gap if you don’t.

If you really believe in what you are doing, you come to the board telling board members what you are planning to do, taking considered advice on whether this is the right strategy, considering that advice and executing on what is, in your best judgment, the right path for the business. That’s what you are there to do. Make decisions fast, don’t fall for analysis-paralysis, trust your gut, execute and iterate. As Tim Ferriss would say, ask for forgiveness, not permission.

Why VCs shouldn’t drive strategy

Guy Kawasaki does lists all the time and it seems to work for him so I thought I would try one too: Here are the top five lighthearted reasons why VCs should not drive your strategy:

  1. We forget 50% of what we said at the last board meeting.
  2. We don’t know the people inside the company and hence have no clue what the team can really execute.
  3. We meet many smart people and hence we have way too many ideas than you can possibly implement.
  4. We are focused on the 5 year vision, yet we are focused on the quarter too — we’re confused.
  5. We don’t need to deliver on it, you do. We come and collect when the job is done.

You want to leverage your board and you don’t want to get fired for being a solo player either. Personally I really like what my partner Jeff refers to as a culture of “champion and challenge”. I guess you have to be born in the USA to say phrases like that, but it’s spot on. If I really disagree with a strategy decision, trust me, we will have a serious discussion about it. But come and champion what you believe in, take ownership, step into the role. Ultimately, I backed you because I believe in you, and you know better.

If you like this post, check out Fred’s blog and his tweets @fdestin. If you want an intro to Atlas, send me an email. I’ll put you in touch if there’s a fit. Finally, contact me if you’re interested in supporting Venture Hacks. Thanks. – Nivi