Entrepreneurial Leadership and Management . . . and Other Stuff


The 10,000th Copy of The Startup Playbook Ships!

The Startup PlaybookAlmost four years ago, we started our two year effort to write the go-to book for first time entrepreneurs. Our reasons were pretty straightforward – we couldn’t find any books available that answered the basic questions that we hear startup founders ask all the time. Other books seemed to be written more to serve what the authors had to sell – venture capital, legal services, financial advice or just their ego – than the founders’ needs. Being founders of many companies ourselves, we wanted to write a book from the entrepreneur’s side of the table. Thus came about the creation of The Startup Playbook.

If we had known what we were getting ourselves into, we may have passed on the effort. It took way longer than we expected. We, essentially, wrote the book three times. Some of the lengthy process was because we knew nothing about writing a book; some of it was that we were perfectionists in the getting down the information we thought new founders needed; and some was taking the time to get feedback from a large number of super helpful beta readers. Also, as we talk about in the book, it’s hard to make a success out of a side gig and the book was definitely a side gig for us.

Yesterday, exactly 18 months since we introduced The Startup Playbook, we “shipped” our 10,000th copy. As it turns, out, that’s the number of copies we set out as our goal. We thought that if we could impact that many entrepreneurs, the journey would have been worth it. We priced it aggressively so that cost wasn’t a barrier – we never even planned to make money on the book – and several accelerators have used it as part of their programs. We’ve learned a lot along the way and have gotten great feedback from or readers. The book was on Amazon bestseller lists multiple times and currently has a 4.9/5.0 rating.

Along the way, we’ve learned a lot. 10,000 was our initial goal, but that’s not where things end. We still talk with new entrepreneurs about the contents of the book and offer guidance along those lines as often as possible. Book sales continue, of course, and we really enjoy the fact that so many people have gotten so much out of it.

Thanks to everyone for all the support of the book. 10,000 is a great milestone, but we have so much more to do!

 August 20th, 2019  
 Books, Startup Playbook, Startups  
 0 Comment

The Startup Playbook

The Startup PlaybookIn The Startup Playbook, my co-author, Rajat Bhargava and I share the lessons, tips and even shortcuts we’ve used in starting, running, advising and investing in companies over several decades. These include tactics for refining your idea, team-building, raising money, developing a product or service, and, ultimately, how to execute.

With a foreword written by Über entrepreneur and venture capitalist, Brad Feld, the book addresses the specific issues and opportunities that founders face as they start and grow their businesses. And, because it’s a window into how founders think about their startup, The Startup Playbook is also helpful to everyone in the extended startup team.

A painful truth of entrepreneurship is that the vast majority of startups fail. There are many reasons for this, of course, but almost all of them come down to the simple fact that new entrepreneurs haven’t yet done and seen enough to have the wisdom required to avoid many mistakes, know what questions to ask and leverage new opportunities.

We share our experiences and what we’ve learned from them in a founder-to-founder discussion style. This isn’t a compendium of what one-hit-wonder founders, VCs and talking heads in the media want you to hear. It’s an in-the-trenches guidebook, written by serial entrepreneurs that is meant to shift the odds of success in your favor.

Even if you’re just dabbling with the idea of becoming a founder and starting this journey, The Startup Playbook can help you to determine whether it’s the right path for you.

You can learn more about it here, or just go to Amazon and purchase it now.

The Startup Playbook Ad

 March 4th, 2018  
 Books, Startup Playbook, Startups  
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Convertible Notes – An Angel Investor’s View


Not so long ago, when one invested in an early startup, it was almost always through the purchase of preferred stock or equity in the company. An exchange of cash for a small percentage of ownership. Neat and tidy, everything on the table, no loose ends. Then, over time, founders (with the help of incubators and accelerators) decided that these equity instruments were becoming too difficult and time consuming, especially with respect to the negotiation of the price of the round and, to some extent, the preferences required by some investors. The “simplified” instrument that most companies started to use was the convertible note.

Convertible notes quickly became de rigueur in the startup community. They are, ideally, debt instruments that offer the investor interest payments in exchange for cash invested in the company. On the successful achievement of certain milestones, the investment (plus the interest earned) is automatically converted into ownership in the company. The key milestone generally being the closing of a subsequent equity investment round. Allegedly, if the company fails to raise an equity round in a specified timeframe, the investor can get their money back. This is supposed to be the advantage for the investor but is, in fact, a useless provision. If the company can’t raise a round, they have more than likely spent all the cash they have leaving nothing in the till to return to investors.

Initially, convertible notes did make things simpler for the founders of the startup. They could kick the valuation discussion down the road and the paranoid founder could withhold any control and financial preferences from their early investors. Unfortunately, these early, simple convertible notes were minefields of problems for angel investors. Foremost among these:

  • They created situations where investors might only get their money back even though there was a large exit for the founders. Think of an exit that happens before a conversion takes place.
  • They did not specify any control provisions or establish a board (every company needs one). No oversight.
  • They often didn’t recognize the level of risk taken by the early investors with an appropriate combination of discount  and conversion restrictions at the next financing round.
  • Because the investment is debt and not equity, they kept the investors from starting the clock on capital gains treatment for the investment until the conversion took place.

To address these problems, investors negotiated new provisions in the notes to patch the holes which, in turn, made the convertible note documents increasingly complex and ultimately created documents at least as complicated as the equity investment instruments that they replaced.

Now, instead of discussing the valuation of the company and specific preferences of the preferred stock in an equity round, the cap on the note (the maximum conversion price), the discount (the reduction in price upon conversion), and the term of the note (when and how conversion takes place) need to be negotiated (some good descriptions of these can be found here).

Convertible note documents have ballooned into multi-page, complex forms that are not only negotiated just like their equity-based brethren, but now carry legal costs that are similar as well, taking away much of the advantage that was sought when they were widely adopted in the first place. In fact, they don’t even succeed any longer at their primary goal of kicking the valuation discussion down the road since the negotiation of the cap on the note has replaced that pretty much 1:1.

The realization that convertible notes are no longer either cheap nor fast has brought about several openly available standardized equity financing instruments like Series Seed, Techstars Open Source Model and others that promise to make a priced round even cheaper and faster than a current, complex convertible note. In my experience, and sadly, these documents are not changing the landscape much.

OK, that’s my rant. For a while, I refused to invest in converts. I wasn’t the only investor around who felt that way, but most didn’t care or push back. The debt instrument took hold and is here to stay. At least for a while. Now, I see very few seed deals that are not structured as convertible notes. Those that aren’t are generally led by institutional investors who often require an equity instrument to do an investment.

There is just so much fighting of the establishment that one can do and, as such, I’ve conceded that if I am to remain an investor, I have to adapt. That doesn’t mean I have to roll over, though. As such, I’ve created a set of criteria for myself when it comes to reviewing the convertible notes of potential investments. There are certain parts of a note that I like to see and some I don’t like. More importantly, there are parts that cause me to negotiate strongly and, ultimately, walk away if they are not added, removed or modified. I’ve tried to outline each of these below.

For angel investors reading this, I’d appreciate if you’d add your thoughts on what I’ve missed and where I’ve overstepped. For founders of startups, I hope you’ll look at these items as guidelines when you’re putting together your note. My intent is not to create an investor-biased instrument, but to fill the holes left by current convertible notes; to shed light on why some terms don’t work well for angel investors and to suggest how to change them so they work better. I don’t believe that any of the guidance I have or changes I recommend should be detrimental to the founders of the company. Speak up if you disagree.

Discount and Interest

Seed investors take a significantly higher level of risk than later stage investors. Let’s face it, the vast majority of startups fail and most of those fail early. In an equity investment round, the risk level taken by angel investors was built into the valuation of the company. Since this is not part of the note, then the investment risk has to be recognized through another avenue. This is the importance of the discount. A discount rate of 20% is pretty standard, but is it appropriate that the seed investor pays 80% what the next round’s investors pay when there might be a year between investment rounds? Probably not. So, the discount rate needs to be judged alongside the cap on the note. The combination of the two should recognize the risk taken by the early investor. That said, a discount rate of less than 20% is pretty big red flag for me.

On interest rates, I usually see 5-6%. I don’t focus on these too much because that’s not why I’m making the investment. Still, if it’s much outside this range, I’ll want to know why.


First and foremost, there must be a cap on the conversion. Again, why should an early investor take the risk of an early investment only to have someone else decide on the actual value of that investment somewhere down the road?

There is no absolute on the cap, of course. It depends on the company’s stage and what’s happening in the overall market. The cap should reflect the projected value of the company at the approximate time of the next financing, discounted to take the risk of the market and execution into account. Good luck with that. Really, it’s the number that in combination with the discount will get investors to fill your round. Hopefully, you can begin to see why negotiating this is no more efficient than negotiating an actual current valuation

Events Prior to Conversion

One of the biggest problems with convertible notes from the investor’s viewpoint is plugging all the potential scenarios that can take place between investing via a note and the conversion of the debt to equity. For example, if the company is sold prior to conversion, does the investor simply get their money back without recognition of the value of their investment? This situation is covered naturally in an equity round, but not in most convertible note documents.

As such, the note must specify that any change of control of the company (aka sale of the company or liquidation event) before conversion has taken place triggers a capped and discounted (as per the terms of the note) conversion into common shares in the company immediately prior to the execution of the corporate transaction. What this means is that the investor’s debt will be exchanged for equity according to the terms of the note, making the transaction a proxy for an equity investment round.

If the transaction is for less than the conversion cap, then the investor should have the right to receive a multiple of their investment. This can be on a sliding scale based on the time between their investment and the transaction. I have seen a fixed multiple of 2X applied to cover this gap.

Closing of the Note

The convertible note should not remain open for a long period of time. Sometimes, company founders will create a note and continue to take money under the terms of the note for an extended period of time. Since the terms of the note represent the level of risk taken and time, generally, reduces risk, it’s not fair for later investors to get the same terms as substantially earlier ones. Therefore, notes should be closed within 90 days of their opening to recognize the risk being taken by the early investors. If a note remains open for a long time, many angel investors will do their best to be the last money in which can make it difficult for the founders to raise the cash they need.

Pari Passu with Future Notes

It used to be that the early seed round was done with a note and the subsequent rounds were equity deals. These days, angels are seeing multiple rounds of convertible notes. When this happens, it’s important that the original note holder ensures that any more favorable terms in the future notes apply to the original note as well. Why should the people who took more risk by investing early receive fewer benefits?

To be clear, this does not apply to retrofitting the terms of an equity investment to original note holders. On conversion, the note holder will become equity participants via the conversion and receive the same terms, with some exceptions mentioned below, as the participants in the equity round.

The Major Investor Clause(s)

Many note documents include a class of investor referred to as the Major Investor. The Major Investor is usually granted rights that include guaranteed information, inspection rights and the right to invest in the next round of funding at their pro rata level at minimum. Effectively, the Major Investor clause(s) give the company and/or investors the right to preclude non-Major Investors from getting information or investing in the next round. As an angel investor, this is a huge negative. If things are going well, I may not have the ability to invest further. I’m not sure how that benefits anyone. No such clause should exist. If it does, I’ll ask for a side letter including me as a Major Investor.

I cover this thoroughly here.

A permutation of this that is regularly found in notes covers what is often known as the Requisite Holders. Sometimes, I’ll find the description of the rights of a Requisite Holder at the end of the note buried in the boilerplate stuff that no one ever reads. Here’s an example:

Any provision of the Notes may be amended or waived by the written consent of the Company and the Requisite Holders.

Where the group of Requisite Holders may be defined as the largest investors in the round. So, basically, certain investors may change the terms of the note at any time even to the extent of making the terms of the note different for each investor. The especially bad part of this, as I mentioned, is that this clause is often found at the end of the note, where no one is really paying attention. Why would I agree to this? Does this serve the company?


Whew! That was long. If you’ve read this far, I hope it was helpful. I’d like to believe that this is a treatise that will reverse the tide of the use and overuse of convertible notes. Of course, I know it won’t. So, at the very least, if this helps a few angel investors be more diligent about convertible note documents and convinces more to push for equity investments instead of debt, then I’ve done my job.

 April 27th, 2016  
 Investing, Startups  

The Dreaded “Major Investor” Clause

I’m a fairly active angel investor. I’ve certainly done enough investing to have seen a broad range of investment paperwork and the preferences of most of the top lawyers used by startups in the country. Generally, the docs are mostly boilerplate. Legally mandated cover-your-ass type stuff. So, rather than wade through reams of paper for each investment, I have key terms that I look for and pretty much ignore the rest. Almost everyone’s intentions are good and all parties involved want all to benefit from the success of the company or to participate equally in its failure. Rarely does someone want an unfair advantage in a deal. Well, mostly.

In about a third of the deals I do these days, I run across the dreaded Major Investor clause. It goes something like this:

“Major Investor” means any Investor that, individually or together with such Investor’s Affiliates, holds at least X shares of Registrable Securities (as adjusted for any stock split, stock dividend, combination, or other recapitalization or reclassification effected after the date hereof).

Big deal, you say, that’s just a definition. True, but why define a Major Investor at all? Because later in the document (usually in the Investor’s Rights Agreement), certain rights and privileges are reserved solely for the Major Investors.

Who are these people? Generally speaking, they are a lead investor in the deal. A single large investor, a family office, a VC, an angel fund or some other investment group. Oh, by the way. Did I mention that the X in the definition above is generally set higher than the level that individual investors are coming into the deal at, leaving the lead investor as the only Major Investor. But, I bet you guessed that already.

What are the rights they reserve for themselves?

  1. Information rights
  2. Inspection Rights
  3. Preemptive Rights (also known as Right of First Offer or Right of First Refusal)

Information rights grant investors the right to receive, at some pre-determined interval, information about the company’s status and finances. Limiting information rights to just the lead investor is just silly. The idea is that it saves the management team time, not having to report to too many people. Why this takes more time than reporting to one party, I have no idea. In practice, it’s just another cc: on the distribution list of the status email.

Some VCs voice a concern that granting such rights to all investors will create a dialog of follow-on questions and comments that will consume too much of management’s time. In my experience, there is almost never much of this going on unless it’s encouraged by the CEO. Often, the angel investors, having mostly run companies themselves, can offer up their situational wisdom when they know what’s going on. This advice is frequently more valuable than the money that was invested.

Inspection rights, which grant investors access to the company’s books, facility and personnel from time to time, is more difficult. I actual agree with limiting inspection rights. This can create a huge time sink for the company and get out of hand when a deal has many investors.

Preemptive rights, which explicitly grant the investor the right to invest his or her pro rata share in the next round of investment is the biggest problem (I wrote about this a while back here). It’s not unusual these days, when a company is doing well and its prospects look good, for VCs to want to maximize their ownership in the company when they decide to invest. Part of this maximization often entails diluting the previous investors in the company. Yeah, that means decreasing the ownership of the angels who invested in the team and idea before anyone was confident of what its prospects were. The one’s that took the most risk. It’s just wrong.

So, Preemptive rights are a protective provision that give early investors the right (not the requirement) to invest more in the company in order to maintain their level of ownership, avoiding dilution. All early investors should have this right, which should be explicitly granted in the investment documents. By keeping this right for themselves, Major Investors are virtually guaranteeing that the angel investors in the round will be screwed in the subsequent rounds of investment if things are going well.

You might ask if this happens in practice. I can assure you that it does. I have fallen victim to this more than once, although not in a while. I know many angel investors who have gotten caught in this trap because they didn’t understand or didn’t take a hard look at the paperwork before making an investment. Recently, I was in a situation where I had to fight to maintain my ownership in a follow-on round even though I had Preemptive rights. The VC investing in the new round demanded of management that all the angels who had previously invested give up their protective right. Several of the angels refused and the deal went through anyway. If there was no prescribed right, you can imagine how it would have gone down.

If you’ve gotten this far, you probably understand my point of view concerning the Major Investor clause. It’s changed my process of discussing an investment with a startup and reviewing the documentation for the investment. My first move is to search for the term “Major Investor.” If it’s found, I check on the rights granted (implicitly precluding the angels in the deal). I don’t really care about Inspection rights and I think that limiting Information rights is stupid, but that won’t prevent me from doing the deal. Preemptive rights is a much bigger deal. I’m simply not interested in making an investment in a company that doesn’t offer me a Preemptive right in return for the risk I’m taking as an early investor. I don’t always invest my pro rata share in subsequent rounds, but I’m not willing to give up my right to do it.

 September 6th, 2014  
 Investing, Startups, VC  
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Handling a “No”

I’ve spent a considerable amount of time playing angel investor over the years which has given me the chance to meet many great entrepreneurs. In general, when an entrepreneur contacts me, he/she is looking for money, advice or both. Generally speaking, I make a quick determination if the people are some that I might be interested in working with; whether or not the idea is something that I can actually add some value too (an increasingly small set of things, as it turns out); and, oh yeah, whether or not I can make any money by investing in it, if that’s appropriate. About a third of the time, I immediately say “no,” because it doesn’t match up with any of my basic criteria.

The other two thirds of the time, I spend more time with the entrepreneur to understand the business as best I can and as quickly as possible. After 35+ angel investments, I should be able to determine the value of a startup quickly, yet, it doesn’t actually seem to be getting any easier. Or, at least, I’m not getting any better at it. Of course, the amount of time I spend coming up to speed with the team depends on my interest and varies quite a lot. In the end, the vast majority of people I talk with ultimately get a “no.” That’s just how the numbers work out. I can’t invest in everything.

In almost all cases – there are those who take a “no” like I said their mother is ugly and are complete assholes about the situation – I do my best to be supportive and helpful in my rejection, explain why I’m not interested and almost always try to connect the entrepreneur up with someone who might be better equipped to help or might be interested in investing. But, it’s still a rejection and it’s tough to take. It’s in how the entrepreneur handles this situation, that I learn more about them than during any of my previous discussions.

Once in a great while, someone will hang up on me or clumsily end a face-to-face meeting with some poor excuse. More likely and if email has been the primary form of communication, I might never get a response to my “no,” which is also a non-response to my offer to hook the person up with another potential advisor or investors. Sometimes, the entrepreneur digs in his or her heals and pushes even harder, thinking that they can force me into changing my mind. Often, pleading, in various forms, takes place.

I’m here to tell you folks, this is all bad. If you’re an entrepreneur (or any one doing business), you should treat each relationship you establish as a long-term, important one. You just never know when you’re going to need it. Sometimes you need it and you don’t even know it – like when another investor calls for an opinion or a reference. I don’t hold a grudge, but I’m not shy about sharing my thoughts about things, especially with people I have an established relationship with (there’s some recursion here, I think).

I’m making it sound like very few handle the situation well. Many actual do handle themselves wisely and professionally.  What do I mean by this?

  • They politely ask “why?” to fully understand my decision without trying to convince me otherwise
  • They thank me for the time I invested and for my consideration of the team and idea
  • They usually ask if I mind if they can engage me for advice or guidance in the future or if they can send updates on what is going on with their new baby.

Yes, for the most part, it’s political and maybe even pandering. It’s also smart. Some people handle it so well, I question my decision not to get involved. Handling it well gives me the impression that the entrepreneur might have the right stuff to be a great CEO. I’ll take that over a great idea any day (although both is nice, obviously). Even if I don’t get involved, that’s what I’m going to tell others when asked.

I’m not trying to be the Emily Post of startup venture engagements here. But handling this basic stuff right can get you very far. There will be MANY more “no’s” in your future. They are always harder to handle than “yes’s.” If you can handle them well, you’ll demonstrate what you can do when things are not so good. A much more important skill than what to do when things are going well. And that’ll get around.

 February 22nd, 2011  
 Investing, Startups  

You Gotta Pay to Play . . . Or Not

Last week, I wrote a post about the right of an investor to maintain their percentage ownership in a company through the pro rata rights provision often found in investment agreements. In that post, I referenced another provision that often crops up, pay-to-play. In its most basic form, the pay-to-play term causes an investor to lose certain antidilution protections if they don’t participate in later financings at a pro rata level. This loss can take a variety of forms. These range from a conversion of all the shares purchased by the investor in previous rounds from preferred to common (ouch!) to the loss of the right to participate in future rounds (a mild spanking).

I get why certain investors want this term in there – if a co-investor is not going to continue to invest in the company in subsequent rounds, why should they retain the rights and privileges of a holder of preferred stock? The same rights and privileges that investors investing their pro rata portion.

I understand the logic, but as an angel investor, I find little to like about the provision in virtually any form. If I, as an investor, supported the company early on and took on all the risks involved with an early investment, why should I ever lose the rights that came along with assuming that risk? That was the exchange at the time – money for some ownership and rights associated with the form of ownership. In my opinion, no future acts (legal, up-and-up ones, that is) should cause the retraction of rights I already have (superseding those rights is topic for another day).

When I invest in a company, I always reserve some money for the next round. Since I generally invest in startups, I consider what a reasonable jump up in the A round valuation might be and hold enough in reserve to maintain my pro rata share in the company through that round. If the A round is a large – dollar-wise – or there are rounds beyond the A round that I haven’t reserved for, I can easily find myself in the position of not having the funds needed to maintain my share. A pay-to-play provision, in these cases, would cause a draconian (yeah, I’m biased) removal of the rights I had already paid for through investment and risk. It just doesn’t make any sense.

I could whine or cry and say that such terms are unreasonable or unfair, but that would be stupid. In the end, I can only do one thing when I run across a pay-to-play provision in  a term sheet, treat it as a big negative in my investment decision. I strictly stay away from deals that go as far as converting the preferred shares of those who don’t invest their pro rata percentage in future rounds to common. I treat as a negative, but don’t always walk away from deals with such provisions that are less onerous. Like I said, I understand why big, later stage investors want this term in the agreement. From my point of view, though, it punishes those who took the biggest risk when the company needed it most.

 November 6th, 2010  
 Investing, Startups, VC  

No Pro Rata Investment Rights?

I passed on an investment this week because the terms of the deal didn’t include the right for investors in the current round to maintain their percentage ownership in the company, through additional investment, in future rounds. This is usually outlined in the term sheet, in legalese, as “Preemptive Rights,” “Right of First Refusal” or even “Right of First Offer.” Basically, such a right simply allows early investors to keep themselves from being diluted in future investment rounds. There is no free ride in this situation, of course, the investor must pay for their pro rata share at the next round’s price, just like everyone else. What was particularly troubling about the term sheet in question was that it was pretty clear that the lead investor excluded such rights from the terms in order to have the ability to flush out smaller, early investors in subsequent rounds of financing.

I’ve seen this before (although less frequently over time) and it boggles my mind. Yeah, if you have a boatload of little investments the cap table can be a bit complicated, but that’s just math. Generally speaking, smaller investors don’t have any strong voting rights, board seats or other forms of control so punting on them doesn’t improve the speed or operations of the company. It’s treating form well ahead of function.

So why explicitly exclude or inhibit any investor small or large from investing in your next round? Are you afraid that you might scare off a large, future investor who doesn’t want smaller investors involved financially? Think about it. Are there rational people who would take this position? If so, are these people you want to deal with? To me, the fact that existing investors want to invest more money to retain their ownership is a hugely positive signal indicating that the people who know a lot about the company have faith in its progress and opportunities for success. As an entrepreneur, don’t you want to encourage such behavior?

By not explicitly giving investors pro rata rights (keep in mind that this provision simply grants the investor the right, it’s not a requirement – I’ll write a post on “Pay-to-Play” term sheet weirdness soon), you not only create a problem in subsequent rounds of funding, but you also create a problem now, in the current round. If, as a potential investor, I fear that I may not be able to prevent my dilution in future rounds, how anxious a I going to be to get involved. I’m not. Thus, my exit from the deal this week.

As my long-time friend and corporate general counsel, Peter Johnson, always says, “it’s, at worst, giving them the sleeves of your vest.” “Them,” in this case, being the investors you want to have involved in the company now and, hopefully, in the future.

BTW, there are loads of resources on the web discussing term sheets from many points of view. I highly recommend you take a look at Brad Feld’s and Jason Mendelson’s term sheet series as a starting point.

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 October 29th, 2010  
 Investing, Startups, VC  

Who Should I Hire?

I’ll take a great team over a great idea in business any day of the week (of course, having both is even better). Why is that? Because ideas are often fleeting – markets change, technology evolves, competition is a moving target and customers are, sometimes, fickle. Great teams can adapt and continually innovate. Great ideas without great teams behind them stagnate.

This is even a bigger problem for startups than it is for established companies. In startups, ideas tend to be in more flux than in mature companies because of the limited time and resources startups have to completely understand the customer. While older companies aren’t immune to these challenges, they are generally not subject to the same limitations.

So, how does any organization hire the right people? Well, starting with a great team helps, of course, but understanding what’s important in expanding it is crucial. Here are a few things to ask yourself when trying to identify the next person you’ll add to your team.

  • Is there a cultural fit? Far more important than having the knowledge required for the job is whether the candidate will fit in with the rest of the team and, in fact be a driver and communicator of the culture you want in you company.
  • Is the candidate a risk taker? He/she should be. Why would you want someone who is going to move slowly and cautiously in your organization. The best people are aggressive in their actions and play offense all the time.
  • Does the prospective employee fear change? Hope not. In fact, the candidate should love change and even seek it out. Many people are afraid of change and even fight it in passive ways, slowing the organization down. If you want a hard-driving, fast-moving organization, you need people who love to drive and be involved in change.
  • Can the candidate work as part of a team? Not only are great people more effective as individuals, but when put together as part of a team, they can virtually make miracles happen.
  • Does he/she have the skills you’re hiring for? Duh. You’re probably hiring because you’re either stretched too thin or you need new skills in the organization. It’s good to thoroughly check if the candidate actually has these.

This is far from a complete list. There are going to be criteria specific to your organization and core to your success that you’ll add to it. The key point here is that hiring the right people is as important as it gets when it comes to running a company or managing any group of people. It’s the team you have that will make the difference in the end and having the best team possible should never be sacrificed.

 October 11th, 2010  
 Management, Startups  
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How Much Should I Look for in My Seed Round?

I often run across early stage companies in a real quandary about how much money to take in their first round of funding. That is, the round just beyond the Ramen noodle eating, avoid starvation round that is usually funded out of your own pocket. The round that really gets things going once you’ve established a team and product viability. The advice they often get – build a spreadsheet outlining fixed and variable costs over the next year or more. Estimate headcount, salaries, rent, capital equipment needs, etc. and, voila, you’ll have your number. That’s fine, of course, but the spreadsheet should be the end result of the planning process, not the process itself. In my experience, there are certain high-level guidelines that should be used to determine how much money should be taken.

Using these, you’ll ultimately have the data you need to plug into a spreadsheet and generate a cash flow estimate – one used for planning AND tracking cash flow – based on the high-level needs of the company and with an eye to future investment rounds.

My thoughts here hold true whether you’re pricing your round or, for the most part, if you’re doing a convertible note. I should also state that this post looks at the question primarily from the entrepreneur’s point of view, although is certainly aligned with the thinking of investors as well. As always, your mileage may vary. This is my opinion and it’s worth exactly what you’re paying to read it . . .

  • Take enough money to securely get you to a step up in valuation. I’m not talking about some marginal increase, but a real increase in valuation – double, triple or maybe even more. What creates that? Usually the achievement of some significant milestone. It’s great if that’s revenue or profit, but a large number of active users or even a major product release are good milestones to increase the perceived value of your company. It depends on what you’re doing. A web service is going to have different metrics than an enterprise software company which will have different  metrics from a hardware company, for example.
  • Take enough money to move quickly, but assume that you will not move as fast as you think you can. Don’t starve the company. Make sure you take enough money so that when you look back over any preceding month of operation you don’t say, “I could have done so much more with $X more.” Additionally, take into account that things will not always go as well as you’d like and, while you’re moving fast, you need to leave some space for stumbling on your way. Map it out as you see it, then add a dash of conservatism.
  • Take enough money to hire the key team members you need – that’s where your leverage is. Never, ever rob yourself of great human resources. Success begins and ends with the level of people you add to the team.
  • Valuation is less important than you think it is. Yeah, this is a hard one to buy into. If your valuation sucks, make sure you’re following the previous guidelines, swallow hard and take the same amount – the amount you actually need. If you are truly uncomfortable with how much of the company you’re trading for cash, go out and look for an investor who will give you a better valuation – but don’t try to do your startup on the skinny, it’s already going to be hard enough to succeed. Keep in mind that your odds of succeeding are not highly correlated with the amount of stock you retain.
  • Leave yourself some runway to close the next round. Many young companies forget this when planning for the uses and needs for cash. It’s unlikely that you’ll have someone at your door ready to write a check the day you run out of money. You wouldn’t want to hand over such leverage to someone anyway. Make sure you have enough money to fund you through the time and effort to get the next round closed – at least 90 days. 120 to be safe.

No, it’s not a science. In the end, the most important part is to get the money you need and to get moving. Time is your biggest competition and it works tirelessly 24/7 to kick your ass. Try not to get caught in abstract notions about valuation. Do a sensitivity analysis, it’s likely to be less important than you subjectively think it is. That’s not to say it’s unimportant, but you should think about what the valuation being offered really means in terms of what you take away from the company given various scenarios. Ask yourself what it is you want to achieve, personally. If the valuation doesn’t seem right after that, move on and find someone else to invest. Otherwise, take the money you need and start executing. And don’t forget the spreadsheet. It really is a good tool.

 July 11th, 2010  

Angel Investing

After yesterday’s phenomenal Angel Boot Camp in Cambridge (MA), I’ve been thinking about a long overdue post on the topic. I did my first angel investment in 1994 and I’m now in the process of wrapping up my 31st (individually, that is, not as part of a fund) – it’s also my third in the past six months. I’ve probably done about 30 more as a limited partner in seed funds and incubators along the way as well. All in, that probably makes me a second tier angel investor, at least in terms of deals done. Third tier if you count the “super angels” who have knocked off hundreds of deals in shorter periods of time. That said, I was recently “voted” as one of Boston’s best angel investors – I think that say’s more about Boston’s investment community than it does about me, I’m afraid.

I invest because I have a blast doing it. It’s about 75% of the fun of running the company yourself with only 5% of the stress. I get to meet smart, energetic people with great visions and boundless energy. It keeps my head in the game, and when I can add value (in addition to money) to help a startup weave it’s way through product, market and management mine fields, I avoid feeling like the least productive member of society for yet one more day.

The difference between a second tier investor like me and the first tier guys (other than brains and talent), is that the first tier investors actually work at finding investments. I’m, dangerously (see below), more passive about it, reacting to the investment opportunities that come to me. I get to see my fair share of of potential deals, but by selecting from a smaller set I not only miss loads of opportunities, but my comparative perspective is likely skewed – the best companies I see may be among the worst potential investments out there.

Fortunately, I’ve been moderately successful with this type of investing. A little over one third of my investments have provided reasonable returns over time with a few big successes doing most of the financial heaving lifting for my “fund.” While my 300 foot yacht with accessory submarine and helicopter remains on the wish list for affordability reasons, I haven’t had much trouble putting food on the table.

While I don’t have any absolutes when it comes to investing, I do have some guidelines that I loosely attempt to adhere to, at least when they’re convenient. Some of them are general and are similar to those used by many angel investors. Others are more personal and, for one reason or another, I’ve picked up over time as a result of my investment experiences.

The general guidelines:

  • “Drill more holes” – I once heard the CEO of Shell Oil speaking with analysts at a conference. When asked how Shell was going to diversify in the coming year, the CEO responded with the statement, “we’re going to drill more holes.” Investing in many companies is the only way to balance the risks of markets, teams and competition. Maintain a relatively large portfolio.
  • Invest in stuff you understand – bright shining objects attract attention (“we have the basis for a cure for cancer”), but the more you know, the less shiny things often look. If you can’t judge the team, market and product relatively thoroughly, it’s probably not a wise investment.
  • Keep some powder dry for subsequent rounds – while the best return in a successful investment comes from investing earlier, holding some cash back to see how the company does and to play alongside any institutional money that comes into the company mitigates some risk and ensures you’re playing on the same terms as the rest of the investors.
  • Everything looks good during the honeymoon – don’t make assumptions that problems you see will go away or that things, in general will get magically better. They won’t. While making an investment, you’re probably seeing the company in its best light. Things will likely get worse before they get better.

My Personal Guidelines:

  • I don’t like convertible debt – the investor takes on an inordinate amount of risk with a convertible note which he/she is generally not compensated for. Think about a note holder who waits 18 months before a conversion is triggered with an equity investment at a higher valuation. For a small percentage (8-10%), the “investor” takes all the risk in funding the company without participating in most of the potential uptick in valuation. Some strange debt instruments are being created now to fill this and other holes, but for all their complexity, the company should just do a seed round.
  • Team over idea – Ideas are cool, but quality teams are cooler. A great team can make a mediocre idea soar or morph the idea into a better one over time. Often, mediocre teams struggle to create success even starting with a great idea. I have to believe that the team can knock the ball out of the park. Only then do I consider the idea itself. As a corollary to this, I need to trust the CEO. Surprisingly, I find this to be a real issue from time to time.
  • There has to be a grownup involved – for all the energy, drive, brains and talent in most startups, there’s often a dearth of wisdom. Someone needs to be involved to provide it and be a sounding board for the startup team. This person or these people, should be on the company’s Board of Directors (check out Every Company Needs a Board of Directors – Startups Too). They can come from inside or outside of the investor group (inside preferable). If I’m the best qualified person for the job, I’ll step up. Usually, though, it’s someone else involved.
  • I hate leading a round – someone has to be in charge of representing the investors in the seed round. Negotiating the fine points of the deal, working with lawyers, getting everything signed, communicating every step of the way, etc. I hate doing it, but once in a while, I draw the short straw. I like investing along side seed or angel funds as a result. They’re pros and do it all the time. It’s not even heavy lifting for them. Most importantly, they’ll do all the herding of the investment cats required. It’s often a real pain in the ass.
  • You can’t and don’t even want to try to tie up every loose end – as much as you’d like everything in the investment to be taken care of, completely thought out and totally bulletproof, it ain’t gonna happen. Stuff is going to change along the way anyway.  The investor and founding team need to feel like they will make adjustments together as warranted.
  • Friend’s before business – this is a personal rule of mine that have broken more than once. Fortunately, it’s never backfired on me. I take both my friendships and my involvement with companies seriously. As such, the potential for conflict is high if I mix them – things never go the way you plan. There are always going to be situations in which the investor needs to support either the company or the management team. Can you support the company over your friend? Your friend over the company? Why even put yourself in that position?

This is hardly a definitive list of any kind, of course, but hopefully it’s a starting point for anyone wanting to get involved in angel investing and for anyone looking for an angel investment. Keep in mind that none of these guidelines have anything to do with the actually business criteria used in selecting an investment. I’ll leave that for another post.

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 June 2nd, 2010  
 Investing, Startups