Questions to help you become investor ready

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I’m a strong proponent of the Socratic method and as such I’m always on the lookout for good questions to ask, especially for the founders I mentor. The Forbes article 15 Key Questions Venture Capitalists Will Ask Before Investing In Your Startup by

I’m going to simply refer you to that article along with a couple of posts of mine. If you can successfully run the gauntlet of all these questions you’ll be ready to sit down with an investor, with confidence!

Here’s another set of questions, Investors questions to address and the post Are you investor ready?

But rather than simply view answering these questions as a one-time exercise I recommend you convert them into a to do list, as it will be highly unusual for a zero-stage founder to have good answers for every question. For example, if you haven’t launched your product you should make sure to arrange for customer testimonials and if you haven’t built a set of KPIs (Key Performance Indicators) there’s a major milestone for your venture. For that one I’ll refer you to my post 12 KPIs you must know before pitching your startup.



How things look from the investor’s side of the table

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Eric Feng, now a VC at Kleiner Perkins, but previously a CTO of Flipboard, founder of Erley and founding CTO of Hulu knows what venture capital looks like from both the founder’s and investor’s sides of the table.

His article A stats-based look behind the venture capital curtain on Medium has an analysis of trends in VC funds in the US over the past 15 years that is highly recommended reading for any founder seeking capital.

From 2003 to 2011, an average of 157 new funds were raised each year. But from 2012 onward, that average rose to 223, or an impressive 42% increase. More funds equals more active investors working at those funds.’

Another insight from Mr. Feng is that all the recent growth in the number of funds raised has been from seed funds, not venture or growth funds.

There has been an even bigger increase in the number of seed investors active in this country because of the disproportionate growth in the number of seed funds raised each year. So if it feels like there are thousands of new investors in the industry, particularly seed investors, that’s because there are.

“A lot of capital does disrupt venture capital, which is the problem we’ve had as an industry.”

— Sarah Tavel, Benchmark

Founders heed well: So even with the sharp influx of seed funds, the vast majority of the dollars are still invested by traditional venture and growth funds. Since 2011 the average number of seed deals per years (4,300) is not about equal to then number of non seed deals *(4,500).

But as veteran VC Bill Gurley says: “Venture capital is not even a home-run business. It’s a grand-slam business.” Virtually every founder I have met with over the past couple of years just assumes they will raise venture capital. However,

As investor Marc Andreessen has said, “returns are a power-law distribution” with the majority of returns concentrated in a small percentage of companies. That’s true now more than ever, and one of the great promises of the venture capital industry that motivates and drives investors.

So while this article is written from the viewpoint of a venture capitalist, it is well worth studying for founders in search of capital. Basically if you can’t show a VC that you have the potential not to just hit a home run, which was good enough the previous decade, now you have to show that you have the potential to hit a grand slam. Otherwise you are unlikely to even get a meeting with a VC, let alone an investment. Yet at the same time there are significantly more investors today than 15 years ago. The size, growth rate, and dynamics of your target market are the gatekeeper metrics for a venture capitalist today. In other words, disrupting a very large market is table stakes. If you are going after anything smaller you need to either bootstrap (be self-funded) or find an angel that falls in love with your startup,

Getting a VC investment has now become much like getting an acceptance to an elite college or university. The strategy is the same, send out a lot of applications and pull every string you can find in your web of contacts to get warm introductions. The only exception to this rule is Demo Day, where you get to present to a mass of investors, alongside your fellow founders. Demo Days are highly efficient for both founders and investors as both sides can cut through the introductory dance to get directly to a presentation or demo of the venture’s product. In higher education the table is tilted in favorite of athletes and legacies – children of alumni. How does a founder tilt the table in the VC game? By being a serial founder! It’s a chicken and egg problem, if you can’t raise money because you never have raised money what can you do? For one thing, find a partner who is a serial entrepreneur. Beyond that close advisors, like your former professors, with deep startup experience can help you distinguish your startup from all the competition.  But keep in mind where you truly need to distinguish yourself is in the minds of customers. If you can do that the money may well beat a path to your door.

Revenue share – an alternative path to financing a startup

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TechCrunch interviewed more than 200 investors and asset managers to gauge their interest in various new ways to fund early stage companies. Their finding? That 63.1 percent were will to explore revenue-based financing.

The concept of revenue-based financing has been around for a long time. It’s relatively straight forward. An investor funds a company and is later repaid by a percentage of the revenue of the company. However, to make this work the company needs to have a predictable cash flow, such as subscription-based businesses. And the company needs to have high margins, so that it can continue to operate whilst paying out a significant share of its revenue to its investor. Imagine you want to buy a bread and breakfast but lack the down payment. You get a loan from the bank for the down payment, based on the revenue that the B & B generates. Assuming that the B & B has a history of a good cash flow business, meaning it has a high occupancy rate and generates enough cash to both pay off its bank loan, cover its operating expenses and generate some profit for its owners this type of deal makes sense for the bank (the investor) and the B & B purchaser (the entrepreneur).

An increasing number of venture funds are now deploying revenue share tools. Novel GP has a $12 million fund that makes revenue  share in SaaS-based companies, which almost always charge their customers on a subscription basis. recently raised their second $30 million fund that invests through a “profit-sharing” structure by which the fund receives disbursements based on net revenue or net income, depending on which is greater. Candide Group, Adobe Capital and the TechCrunch affiliated fund VilCap are additional examples.

However, there are a number of issues with revenue share financing, for both the investor and the founder. For the investor, the author’s calculation on a hypothetical revenue share investment in 30 companies on average it would take about 4.4 years to realize a 3X return on the initial investment amount of $20k, to $100k. But how many startups can get off the ground on that amount? That’s about what the average founder can raise from friends and family on a convertible note.

Not only does the recurrent obligation to pay the investor shrink the pool of capital available to reinvest to grow the business, other investors who aren’t familiar with the model may be scared away, as were several investors interviewed by author Allie Burns.

And even if you add up all the capital under management of all the revenue share venture firms, I doubt it even comes close to approaching the average size fund of a single traditional equity VC fund. So it seems like founders would be going after a small amount of capital from a very small number of investors.

… based on the experience of VilCap Investments and other practitioners like Candide Group, we’ve found that revenue-share financing is generally only appropriate up to a certain size of investment, generally between $50,000 and $500,000, depending on the expected return multiple and timeline, and the company’s annual growth rate and traction at time of investment.

So while it’s encouraging to see alternative forms of investment available to founders, in reality it’s only a very small number who will be a good fit for this model. My advice would be it would probably be a better return on time invested to study crowd funding, especially since the SEC’s changes to rules governing investors have changed recently. No longer must an investor have a net worth exclusive of primary residence of $1 million dollars or more or an annual income greater than $250,000 to qualify as an accredited investor. Check out the Regulation Crowdfunding page of the SEC’s web site. And while you are at it you might want to review the Exempt Offerings page, which explains the exemptions from registration that are most frequently asked about.

Under the old regulations the SEC forced any company with 500 investors or more to go public, which basically shut down crowdfunding. Now that is no longer true, and unlike revenue share, crowd-funding is a new flavor of equity financing, something all investors understand.

Things you should know about VCs

vcThere are lots of myths out there about VCs, about how they will take over your company and replace you as CEO or that getting a VC investment paves the way on your path to riches. But Jason Lemkin of SaaStr, the world’s largest community of SaaS executives, founders, and entrepreneurs, has an excellent article on some facts you should know about VCs – forget about those myths!

  1. Entrepreneurs tend to think about VC firms, but in reality VC firms don’t do investments, individual partners at VC firms are the ones making the investments. Just like medical device makers don’t sell to hospitals, they sell to the individual financial decision makers in departments in hospitals that need those devices. And the hard truth is that partners at VC firms do very few investments per year, typical just one or two. So as a collective firm they may do a significant number but the individual partner who’s a potential fit for your firm only one or two. So you need to have a really compelling fit for that VC and you better know from your research which partner in the firm might invest in your firm. That knowledge should be based on their track record, blog posts, social media presence, and G2 you can gather from their portfolio companies.
  2. As the Bob Dylan song goes, “Everybody gotta serve somebody” and in the VCs case it is their limited partners, those pension funds, college endowments, and wealthy individuals who invest in venture capital as part of their diversified investment portfolio. So check out the limited partners, for example, when we were talking to Greylock about funding Course Technology it turned out they had six or seven limited parters which were college and university endowments – so they were excited to invest in our educational software and publishing company.
  3. Partners are diversified, you aren’t. Unless you are Elon Musk or Jack Dorsey, chances are very high that the only company you are fully invested in is your own. Not so for partners in VC firms. In essence they are portfolio managers; your firm is just one amongst several in their portfolio. So they will tell you that their interests are fully aligned with your’s but in fact they are not. Resources – money, connections, and their attention – will go to only those firms in the portfolio that they perceive as the winners.
  4. VCs don’t just make money on exits, they make money on management fees. And to make a lot of money on management fees – typically 2% of funds invested per year – they need to raise multiple funds. And they raise those funds by getting step ups on the valuations of the companies in their portfolios. Yes these are paper gains but they can show their LPs strong IRR on their current investments. So VCs always have one eye on the next fund and how they will raise it.
  5. Small VCs Align With You, But Lowball You.  Big VCs Don’t Align As Well, But Can Pay More. Big VCs can write big checks and they also can hold funds in reserve, so they can participate in multiple rounds without getting diluted. But small funds will probably have to syndicate their rounds – share the investment and any returns – with other firms. Big VCs can write very big checks, but then they need to have a big return to impact the fund. And partners can only serve effectively on just so many boards – typically no more than seven to nine – so if you only need a small amount of funding they can’t afford the opportunity cost of taking the time and attention to invest in you, let alone serving on your Board.

Entrepreneurs have learned about product/market fit, but investor/venture fit is equally important. The amount you need to raise, the market you are targeting, how you play with the partner’s portfolio, and your need to raise multiple rounds to get to breakeven are all factors you need to take into account before you even start contacting VCs. As Sun TZu wrote in his work The Art of War, “Every battle is won before it’s ever fought.”

10 key steps in approaching your first VC


If you are indeed investor-ready, then it’s time to take these key steps before you approach your first venture capitalist for an investment. And you do have a warm introduction to this VC, right? If not, go back a step and get one!

  1. Review the investor’s portfolio, which is virtually always on their web site. Are any of these companies competitors to you or potential competitors? If so, you should steer clear, as the only reason you will get the meeting is to have their partner gather information about you, for them.
  2. Are you at the right stage for this fund? Some funds primarily do follow-on rounds, they virtually never do seed stage. Make sure you are at the stage that is a fit with your target investor.
  3. Is the timing right? VCs, like founders need to raise capital. You don’t want to target a firm that’s closed out their first fund and is in the middle of raising capital for it’s next fund. Or a firm that has invested virtually all of its fund already. You may need to ask the partner the stage of their fund, this is not publicly available information.
  4. How much runway do you have? It can take 6 months to raise an institutional round. You might need to raise friends and family capital first, if you haven’t already. Or perhaps you start with an angel round. The cardinal sin in startups is to run out of cash! And you don’t want to be negotiating with a VC from a position of weakness because you cash is about to run out.
  5. Brief your team. They should know what firms you are approaching and which partner in those firms. You never know when a VC’s path will cross with one of your team’s.
  6. Create a killer two-sentence summary of your firm to go in the body of your email.
  7. Create an exciting one page summary of your business, including the team, your market opportunity, and secret sauce. Don’t forget your contact info!
  8. Come up with a good subject line for your intro email. Such as “Bill Jones recommended we talk with you” where Bill Jones is the person giving you a warm intro. Obviously, if he’s gone as far as sending you both an email, then the subject line would be “Following up on intro from Bill Jones.” VCs get a lot of email! Don’t let yours get lost due to a vague subject line.
  9. Do not send your pitch deck. Even if they ask for it. Politely explain the deck has been designed to support your presentation, not stand in for you. You want to use the one-pager to get the investor meeting, where you will be glad to present the deck. If you really want this meeting and the VC is adamant about wanting your deck first, you can one of two things: one, walk away. That may actually impress the VC; or two, craft a more detailed deck that can standalone as a document presenting a complete view of your business. But keep in mind, decks get passed around, do you want that? Better that your one-pager gets passed around.
  10. Do not specify how much money you are asking for! It may be too much for the fund you are targeting or even too little. Don’t give them the opportunity to use that excuse to ignore your email or follow up phone call. Once you get into the meeting your ask will be the last slide in your deck.
  11. Last and probably first: talk to some founders who have received funding from this VC. Do they think you are a fit with their fund? Do they recommend the VC? And most important, how does the VC act when times are rough? Read my post Founders need to perform due diligence on prospective investors.

So we’ve done it the Spinal Tap way, turning up to 11! There’s more to say, such as rehearsing for a phone call to or from a VC, but we’ll stop here so you can get going.

Pros and cons of investing in your own startup


Lessons from my own experience

I recall being told by VCs not to invest in my own companies. Investing should be left to professionals (e.g. venture capitalists), founders should focus on building their companies. I’m sure that there is some self-serving in this advice as VCs want to buy the biggest slice of a company they believe will be successful. If founders self-finance they may have less need for VC funds. On the other hand, the advice from angels was just the opposite. They want to see founders’ skin in the game. They are suspicious if you don’t invest in your own company. “Why should we invest in something you won’t invest in?”

I managed to get through my first four startups with only VC funding, no self-funding, no angels. But once I dropped out of the major leagues, which I did after leaving
Mobile-Mind and went into the minors to work on a mobile shopping app that was funded mainly by my partner. He did inveigle me into putting a small amount into the venture, which I ended up losing, as the world wasn’t ready for a mobile shopping app in 2002, duh!

Unfortunately, I did not learn my lesson with SmartWorlds and cajoled a friend and former successful VC into us self-funding a startup based on his idea. This was a great idea, it became Stories for Instagram. But we didn’t have the Instagram platform to launch this early version of Stories, so like the mobile shopping app, we belly flopped. But my biploarity had its switch flipped still in manic mode, so once again I tried to start a company with my own idea, as I did with Throughline. While we had a modicum of success with Throughline, our investors lost confidence in us and were afraid of our entrenched competitor, so we shut down the company.

I should have learned that my role in the ecosystem of startups was to help visionary founders build their companies – I have no sense for what’s commercial, so the visions I had for Throughline and PopSleuth never gained traction. But fool that I was I put my own money into PopSleuth, which was created to help solve my own personal problem: how could I keep up with the latest releases and appearances by my favorite creatives -writers, directors, actors, authors, and musicians? I believed in the idea that successful entrepreneurs built products to solve their own problems, like Dan Bricklin who invented VisiCalc to save himself the labor of trying to revise financial models using just a calculator in his Harvard Business School classes. It is true that many successful startups were founded to solve the founder’s problem, that doesn’t mean you will be successful just because you are creating a product to solve your own problem.

So after being burned twice by investing in my own startup ideas, I’ve gone to the sidelines to coach other entrepreneurs. And often the subject of self-funding or funding via friends and family come up.

I advise them founders that:

1.  self-funding should be a last resort and a bridge to either shipping your product or bringing in outside investment.

2. You should not invest more than you or your friends and family can afford to lose.

3.  Only if you plan to raise angel capital will self-investment be a plus, otherwise it won’t help you gain institutional investment.

4. If you do bring in substantial outside investment odds are you will get very diluted by the time you exit the venture, so what good did that self-investment do? (see number one).

The best capital is not your own capital, it is not investor capital, it is customer capital. Bootstrapping to build your product is the best way to go. Even if customer revenues are slow to take off your venture will be far more investable with a complete product and some customer revenue.

So basically there are only two pros to investing in your own startup: it acts as bridge to outside capital or customer revenue or it helps persuade an angel or angel group to invest. Unless you have made substantial money from a previous startup or have inherited wealth, your investment probably won’t represent meaningful equity after a several rounds of investment. You would have to continue to invest your own money in these rounds to maintain your equity share. I don’t know anyone who has done that.

Blood, yes. Sweat, yes. Tears, yes. Your own money, in most cases, no. Bringing in outside money is real validation you have a viable venture; investing your own money validates nothing.

Lessons from Jean-Louis Gassée, former VP of Software Development at Apple, and founder of Be Computing

For another tale of investing your own money, read Jean-Louis Gassée’s Monday Note50 Years In Tech. Part 16: Be Fundraising Misadventures. JLG paints a very accurate picture of the difference between professional investors and amateurs, i.e. founders like himself.  You have to be a fan of the history of computing like me to read all 16+ parts of JLG’s history. But I do highly recommend part 16 for anyone contemplating investing their own capital in their venture. Here’s a few tidbits:

I wanted to keep Be out of the vulture capitalists’ talons, so to fund the company in its early years, I put my own money into the venture. That was the first of a series of fundraising mistakes.

…I thought I was doing the right thing, but, as I found out, professional investors in the US are suspicious of self-funding. They prefer a clean division of labor: The entrepreneur provides the idea, the psychic energy, the leadership; the pros supply the financial fuel.

When my personal coffers began to run low, I accepted investment money from friends and business acquaintances.

JLG’s note does a good job of listing what he calls the Laws of Professional Venture Investing. If you don’t know them, I’d advise you learn them before you start your venture.



Are you investor ready?


Today is the deadline for applications to MIT’s Demo Day to be held in April. Demo Day gives selected Venture Mentoring Service founders five minutes to pitch to the audience of VCs and angels.

I work almost exclusively with raw startups, whether at MIT VMS, The MIT Sandbox Fund or the MIT Post-Doc Association. Very, very few founders want to rely on bootstrapping, the vast majority have “how do I raise money?” on their agendas early in the mentoring process.

But what I find is that few new founders understand what it means to be investor ready. Here’s a snapshot of what is needed before you decide to apply for investor pitches:

  • Team – most investors I’ve known focus on the team first. And in fact of the team, 90% of the focus is often on the CEO. Does she or he have what it takes to drive a company to a $100 million sales run rate? Or will the investors need to replace the founder with a seasoned veteran as the founder either can’t handle running a company with several hundred employees, or is often the case, is not really interested in doing so. They prefer to build things, as most founders tend to be engineers and engineers build stuff. So you need a CEO who presents well: confident, articulate, and passionate about the business, with a vision for how they will disrupt an existing market or create a new one. While investors don’t expect raw startups to have full teams, it’s tough being a singleton. At minimum you need a partner who complements, not duplicates, the founder’s skill set. Too often I see two engineers, a CEO and a COO – both are makers, not sellers. While it’s usually too soon to attract a proven sales person, early stage startups have to show that the founders can sell. We used to call that “executive sales.” Even when a startup hires sales staff often customers or clients need to be closed by the CEO – they want to know who is running the company they are betting on.  A good two-some is an engineer and an experienced digital marketer. A three-some might add someone with business development experience – building partnerships that turn into channel sales.  Teams whose members know each other previously and/or have worked together tend to be more successful than strangers brought together through networking events.
  • Product – investors want an unfair advantage, as one veteran VC told me. What’s your unfair advantage? These days with so many AI startups that advantage may be an algorithm or patent pending technology.  Secret sauce is hard to manufacture. But differentiation isn’t. How are you different than other products or services targeting the same customer? What is your sustainable competitive advantage? What is remarkable about your venture? The downside of today’s entrepreneurial explosion is that there may be a raft of competitors, no matter what niche you choose. And first mover advantage is not always that. But if you can’t demonstrate – show, don’t tell – a clearcut differentiator that will appeal to customers don’t bother apply to demo days. The stage of your product is also vitally important. The best is that you’ve launched and you not only have traction, but you have viral growth. That’s pretty exceptional and but a few very smart MIT founders have even raised money with just a prototype. But the further along the product lifecycle you are and the closer you are to building a customer base, the better.
  • Market opportunity – far too many founders want to boil the ocean. If you suggest they target a niche to start off they get visibly anxious that they will be leaving millions of customers behind. Quite the contrary, if you can dominate a niche you can then move into adjacent markets. Facebook’s classic rollout started with Harvard, then other Ivy League schools, then other elite colleges then to anyone with a .edu email address and so on. Mark Zuckerberg was careful not to make the mistake Friendster made of having so much demand their servers failed repeatedly. VCs want billion dollar markets and your market needs to be growing, not static nor shrinking. The better you can explain your market dynamics and how your solution will win against competitors or whatever customers are getting by with, the better.

VCs are all about managing and reducing risk, contrary to their popular image as swash buckling risk takers. There are three types of risks: management, technology, and market. To be investor ready you should be able to convince investors that you have significantly reduced risk in all three areas.

There’s one other intangible to being investor ready: capturing investors’ imaginations. While these Ivy League MBA-wielding financial managers pretend to be data-driven, they really go with their gut (and often what their kids say about consumer apps) and then justify their decision to their partners with the numbers. I have found one key way to know that you have captured an investor’s imagination: when they start telling you what new markets your product could conquer. A truly excited investor buys into the vision and will demonstrate that by throwing out ideas on how you can make you product even more successful instead of their default mode of strafing the poor founder with a fusillade of reasons why their venture will never work.

So run through the big three – team, product, and market opportunity – and if you think you have critical mass in all three areas go for it, otherwise get back to work. Don’t worry, investors will always to be out there and interested in a world-class team with a breakthrough product, solving a big problem for millions of customers.