We all know that every startup is risky. No risk means no reward. Yet every investor has his own “rules of thumb” on what makes a specific startup too high a risk for his investment taste. You need to know these guidelines to set your expectations on funding.

Of course, if you intend to fund the business yourself, or have a rich uncle, external investment funding concerns are not a problem. Yet, it’s still worthwhile to understand the issues so you can minimize your own risk of failure. Here is a summary of the “big picture” high risk considerations:

1. Inexperienced team. I’ve said many times that investors fund people, not ideas. They look for people with real experience in the business domain of the startup, and people with real experience running a startup. An expert in software is considered high risk in manufacturing, and a Fortune 100 executive running a startup is high risk.
2. Historically high failure rate category. Certain business sectors have historical high failure rates and are routinely avoided by investors. These include food service, retail, consulting, work at home, and telemarketing. On the Internet, I would add new social networking sites, and new matchmaking sites.
3. Dependent on government regulations. If your business model is dependent on government approvals, that can take a long time, or require political connections. All new medicines, for example, require expensive and extensive testing for side effects before FDA approval. Of course, successful approvals may also mean high returns.
4. Large initial investment required. If your startup involves new electronic chips, that may require a huge investment (more than $1B) to ramp-up manufacturing. By definition, all but the largest investors will pass, and it becomes high-risk to all investors. New drugs often fall in this category, due to long clinical trials and FDA approvals required.
5. Businesses with small return potential. Businesses with a low growth rate or a small opportunity (less than $1B) are considered high risk by investors, who get measured on portfolio return over time. That eliminates from consideration family businesses, small niches, and business areas with declining growth.
6. Poor public image businesses. Most investors like to maintain a squeaky clean image, so would consider it high risk to invest in businesses on the margin of legality or social acceptability. Don’t expect investor enthusiasm for your gambling site, porn site, gaming, or debt collection business.
7. Operations in another country. Investors in one country are generally reluctant to invest in a company outside their realm of operational knowledge. We all know that the success “rules” in Russia are different from the USA, so cross-boundary investments are considered high risk, even if you have operating experience there.

These rules of thumb should not be viewed as barriers, but just another factor that needs to be addressed specifically in your business case and investor presentation. It’s better to be proactive on these, rather than hope your investor is too naïve to notice. Your challenge, if your interest is in one of these areas, is to point out quickly why the high risk is mitigated in your case.

In summary, it pays to have some insight into how investors will likely see you, since this allows you to prepare the best case, both for your own decisions, and for approaching an investor. It’s never smart to switch your plans to a “less risky” business that you know nothing about, because your lack of experience there simply moves that alternative to the high risk category.

If you can’t handle risk, don’t do a startup. But even if the risk energizes you, do it with your eyes wide open. Even the best adventurers do their homework before starting down a new path. Known obstacles are a lot easier to overcome than surprises. Enjoy the challenge.

Startups are usually so focused on selling more of their branded product or service to their own customer base (organic growth) that they don’t consider the more indirect methods (non-organic growth) of increasing revenue and market share. Non-organic growth would include OEM relationships, finding strategic partners, “coopetition,” as well as acquisitions.

This initial focus is usually driven by limited financial and people resources, as well as the bandwidth of the executive team. Yet a creative and skilled team will often find that non-organic growth techniques can better leverage these limited resources.

An example of a startup which used non-organic growth early and effectively was Microsoft. Bill Gates started producing software solutions, like his Basic Interpreter and MS DOS, but quickly focused on adding thousands of small partners for applications, and major partners like IBM and other hardware manufacturers. Even mergers and acquisitions (M&A) came early.

Some people feel that organic growth is “better” because it requires real innovation and sustained effort to create long-term competitive advantage through differentiation and efficiency. They might agree that it cannot compensate for the speed and scale of growth of the non-organic approach, but has lower risks of failure.

Despite the risks, there are many advantages of non-organic growth, even in startup environments:

• New product or service lines. Organic growth assumes innovation in the product or service, but non-organic growth through white labeling and strategic partners may add totally new brands and services to your revenue stream.

• Fresh customer base. Teaming with another company, or buying another company, can add new geographical locations and new customer segments to the business. These relationships need not require cash investments; often they are done with exchanges of equity or assets.

• Economies of scale. In many cases business opportunities with competitors (coopetition) will open up a new marketing channel, and definitely give you the cost advantages of scale. Economies of scale also apply to marketing, distribution, and sales.

• New management skills. New business relationships mean new perspectives and new executives working on the opportunity. This can be a significant competitive advantage over major competitors, and overall reduces competition in the market place.

I’m certainly not proposing that one mode should be used to the exclusion of the other. Rather, I recommend that you pursue both concurrently, per the advantages of each. For example, if you are in an industry which is fragmented or has a slowing growth rate, with too many competitors, non-organic growth may be required for survival.

Use organic growth options for things which you do best, where there is plenty of room for growth by selling your products in new geographic areas, or using new sales channels, such as through a wholesaler or website. Organic growth is typically safer because you’re using a tried-and-tested business model, and you can reinvest profits back into the business.

Certainly non-organic growth has its pitfalls. Entrepreneurs, while partnering with or acquiring a new business, must check for compatibility and strategic fit. Yet startups looking for investors need to evaluate all the growth alternatives from the very beginning. “No growth” or even slow-growth companies waiting for an angel may have a long wait.

Every time I hear about a new startup that is in stealth mode, I wonder what problem they are hiding from whom. Of course they pretend that they are trying to avoid alerting competitors prior to launch, but too often it becomes an excuse to move slowly in a world that’s all about getting to market fast.

I believe stealth makes sense for large companies who can be sued for “pre-announcing” a new product to stall the market or kill a competitor. It also makes legal sense to never disclose the details of your patent application, before the product is ready to ship. But otherwise, startup companies should seek out publicity and the open sharing of information, from day one.

Openness is part of the business culture of entrepreneurs and technology centers around the world. People talk to people, and even competitors freely exchange news on trends and discoveries. Here are seven ways this can actually help your startup efforts, rather than hurt them:

1. Initiate media interest. These days, new technologies and social trends are fanned from an ember into a flame by the media and word-of-mouth. This takes time, and is more valuable than any advertising you can buy. It’s probably here that you need the “first-mover advantage” more than in the lab.
2. Get concept feedback early. No matter how good you are, your initial idea is likely to be at least partially wrong. The sooner you get that feedback from people who count, the better your chance of recovery, and the less money you have wasted. Don’t be so arrogant to assume you won’t need course corrections.
3. Find your real competitors. The sooner you disavow yourself of the notion that “we have no competitors,” the more likely you are to survive. “No competitors” may mean no market (give up now), or customers are happy with alternatives (keep their car rather than ride the new fast train). Face reality early, and you can deal with it.
4. Deliver minimum product and iterate. Stealth mode can give you a false sense of security that you can take additional time to get it right the first time. Time is your biggest enemy, and customer feedback is your biggest ally. A startup that has been incorporated for two years or more without shipping is already seen as a bad investment.
5. Prime the investor world. Don’t talk directly to potential investors until you have the business plan and other basics complete. But start networking with advisors, industry pundits, and domain experts early. Your direction will get back to potential investors, and create a sense of heightened expectations that can help you get in the door when ready.
6. You need time to pivot. The good news is that almost every mistake can be undone, if you have the time. Customers are more forgiving of early visible changes in direction, and the cost is much lower for you. With stealth mode, you can’t learn early enough to pivot gracefully.
7. Tune your website. Most startups need funding before shipping, and investors expect to see your website to validate your business plan. In addition, a website needs several weeks of presence for indexing by search engines, search engine optimization, blog activity, and link building. These things can’t be done while in stealth mode.

To enforce stealthy behavior, startups often require everyone, even potential employees to sign nondisclosure agreements, and strictly control who may speak with the media. This is a turnoff to everyone, and real investors never sign nondisclosures. It’s all an expensive distraction that doesn’t work.

Overall, I recognize that there are some startups, like biotech and semiconductors, with long highly technical development cycles and huge competitors, where early stealth makes sense. With most others, like web services, incubation time must be short, and secrecy can be the kiss of death. For these startups, stealth mode can keep you under the radar, just when you wish you could be found.

Wouldn’t you like to be one of the lucky people who joined Google and Microsoft when these were startups, and now be a multi-millionaire? So people ask me “How many shares should I ask for when I join a startup today?” In reality, the number of shares doesn’t mean anything – it’s your percent of the total that you need to negotiate.

For example, 200,000 shares may sound like a lot, but if the startup has issued 20 million (a common starting point), that’s just 1% of the company. By the way, you will normally only be offered “options,” which vest over a 4-year period after a 1-year “cliff.” That means you will get none of these until after you work for one year, and the total only if you stay for four years.

Plus you have to remember that these 200,000 shares could still be worth nothing in four years, depending on the “strike price” today, compared to the market price four years from now. Many employees forget that there isn’t even a market for stock, until after the company has gone public, which hasn’t happened to many companies in the last few years.

Thus, stock doesn’t “pay the mortgage” today, so to speak. Unless you have a sizable nest egg, or a working spouse with an income to support you, I would recommend that you consider any stock options as a “bonus,” rather than a key part of your compensation for joining a startup.

With all that said, here are some “rule of thumb” guidelines on what might be a reasonable offer, as extracted from an old article by Guy Kawasaki, and based on discussions I hear rattling around the investor community.

• CEO brought in to replace the founder, 5 – 10%
• CTO, CFO, VP of Marketing or Sales, 1.5 – 3%
• Chief Engineer or Architect, 1 – 1.5%
• Advisory Board Member, 1%
• Senior Engineer, .3 – .7%
• Product Manager, .2 – .3%

If you are not on this list, just worry about getting whatever your peers are getting. It never hurts to ask in a job interview what stock options are available, and don’t accept an offer which promises to “work out the equity terms later.”

Obviously, what you get will vary depending on what you bring to the company, and what the market will bear. The numbers I mentioned don’t have a level of precision that can be associated with a particular geography, or a particular business type. Offers near the high end of a range will come with a lower cash salary, maybe even 50% of the going rate.

Any offers of equity compensation before the first round of institutional capital should be considered purely speculative. You should also assume that your percentage will go down through dilution as the company raises additional rounds, and offer sizes will go down as the company grows.

Your compensation is the total package, stock plus salary. At best, you should view stock as “deferred compensation” or a “bonus,” which has no value today, and a risk for the future that is much higher than mutual funds, or a conventional balanced public stock portfolio. Yet it has been a source of great wealth to a tiny percentage of people.

Couple all this with the fact that working at a startup is much tougher than working at bigger companies – despite all the hype you see about startups which provide free food, pool tables, and totally flexible hours. Generally, less structure means more stress, and fewer people means higher expectations, longer hours, and a job that may be gone tomorrow.

The bottom line is that you shouldn’t even think about joining a startup, stock or no stock, unless you believe in it and are ready for the adventure of your life. It will always be a learning experience, but it may be a bumpy ride to nowhere. How many gamblers do you know that have won big?

One of the hot new approaches I have seen around the country for assisting startups looking for funding has been “crowd-sourcing” sites (Kickstarter) or “crowd-pitching” events (Funding Universe). These are variations on a “crowd-funding” theme to raise money for a startup through social networks and voting at public events. I’m still waiting for a startup to proclaim real success from this approach.

Crowd-sourcing tools, usually Internet applications, use the social media to poll for interest, feedback, and ultimately some funding for the startup. This is a complex task, especially as it involves creating an accurate yet compelling offer, collecting the money, and rewarding the investors.

Crowd-pitching is an offline event, but logically similar, which give several candidates an opportunity to pitch to a crowd of interested people for a couple of minutes, after which the crowd “votes” with some play-money to pick the best candidate, who then wins some nominal investment amount or services.

Certainly both of these crowd-funding approaches provide the entrepreneur with an opportunity to hone his pitch, and get some real consumer feedback on the idea. But from my perspective representing investors, this approach falls short on several counts:

1. Focus is on the product, not the business model. When pitching to consumers, online or offline, the feedback will likely be on features and design. The key success factors of the business model (how you make money), management expertise, and financial projections will likely get overlooked.
2. Amount of funding provided is very small. The amount of time and money required for publicity and promotion of any crowd-funding activities may be more than the return. In reality, a few hundred or even a few thousand dollars to a few winners, is probably not a return on the investment required.
3. Multiple micro-investments are not manageable. Investors know how tough it is to get a set of terms accepted by even two investors, much less hundreds. The administration of legal conditions, signatures, disclosures, and distributions is a nightmare. In my opinion, that’s why micro-finance has rarely worked, even for loans.
4. Proposal content is too short to be meaningful. In all cases, to keep non-professionals attention, the content of the offer online, or pitch presented, is very limited. No one contemplates including a business plan, investor presentation, or even the equivalent of an executive summary.
5. Crowd sample size and makeup not representative of market. If the pitch is offline, the audience is likely to small and mostly budding entrepreneurs. Even online, the type of people who may respond to social media requests may bear very little relationship to the intended market.
6. Investors are not prepared for the high risk of startups. Crowd-funding investors are not constrained to be accredited professional investors. They may not understand that nine out of ten startup investments provide no return, and the risk of securities law violations is very high.
7. Intellectual property is jeopardized. Non-disclosure agreements can’t be done in these environments. In an environment populated by entrepreneurs rather than investors, when you are new to the game, you are exposing your plan to your biggest potential competitors.

Some groups are making an effort to mitigate these problems by pre-screening the candidates, and providing an experienced panel of investors to do the judging. This helps by making sure the feedback is realistic, and the presenters have a rational business opportunity to present. I’m already working with a couple of organizations along these lines.

Overall, there is no question that crowd-funding makes sense for non-profits soliciting donations, disaster relief efforts, political campaigns, or even artists seeking support from fans. But in the competitive world of “the next big thing,” with millions of dollars at stake to be lost, counting on these mechanisms today for money would be foolhardy.

Investors are people too. They evaluate you like you should assess a possible co-founder or first employee. What are your credentials? What have you done that would convince me that my money is safe in your hands? Only after they see you as fundable, do they want to assess your plan for fundability, not the other way around.

Even with great credentials, it is all too possible for an entrepreneur to come across as a high risk investment. Here are some “rules of thumb” that indicate a marketable and experienced entrepreneur:

• Highlights team strengths, more than his own. Some entrepreneurs seem to never stop talking about themselves, and all their accomplishments. The best ones talk more about how they have assembled a well-rounded team, and will continue to fill in the gaps.

• Talks about the implementation plan, not the idea. Most entrepreneurs are great at envisioning their business idea, but the implementation is fuzzy. Experienced entrepreneurs talk about their implementation and rollout plan, with real milestones and quantifiable results.

• Customer needs and benefits first, then product features. The best entrepreneurs show that their market domain knowledge is as strong as their product technology knowledge. They are able to weave their solution into the market, the opportunity, and customers, in a way that sounds like a natural fit, rather than a product sales pitch.

• Focus is clear, not all over the map. Success means the entrepreneur must be laser focused on driving the business, passionate about a product, and passionate about a specific set of customers. If the business plan reads like a smorgasbord of offerings, there are probably not enough resources to do any well, and customers will be confused.

• Rational business model, with prices and volumes. Unless the business is a non-profit, the entrepreneur needs to show how he will make money. The days are gone when investors want only to see a large market share or growth in eyeballs. Are revenues and costs reasonable and projected for five years?

As an entrepreneur, don’t let your ego get in the way, or believe you can take the world on by yourself. If you want to attract investors, you must be willing to listen and work with others, as well as share your ideas or your knowledge. Loner entrepreneurs won’t get their foot in the door with any investor I know.

If you are young or inexperienced, and don’t have business credentials yet, don’t hide this fact. I recommend a proactive approach, to highlight the accomplishments you have, the power of other team members, and show some humility in admitting a search for the rest of the team.

So you might ask, how do first-time entrepreneurs ever get the funding they need to prove that they can perform at the next level? The best answer is to team yourself with someone who has “been there and done that.” After a team success, you’ll find all members are “promoted” to the next level.

Another common approach is to bootstrap your first startup to success, possibly with some help from friends and family. As I said in the beginning, investors are people too, so get out there and make them your respected business friends before you try to sell your idea. Business networking is not the same as cold calling with a hard sell.

Every investor knows a few good entrepreneurs, like Marc Andreessen of Mosaic and Netscape fame, who can get millions of dollars of funding for just about any idea, but I don’t know one investor who has funded a “million dollar idea” without regard to the person and the plan behind it. Think about that the next time you pitch your idea.

One of the toughest and yet most important questions you will be asked by savvy potential startup investors is “What is your sustainable competitive advantage?” Yet many entrepreneurs, maybe in their passion for their new product, gloss over this one, or even announce that they have no competition.

Think about each of the three words for the full meaning of the phrase. “Sustainable” means over the longer term – not just today. First to market, for example, is not sustainable. It may buy you a few months, but if you show traction, competitors with deep pockets will catch up and bypass you quickly, jeopardizing all your investments.

“Competitive” should be taken broadly to include alternative ways that people might solve the problem you are addressing. Don’t define your scope so narrowly that you would not consider airplanes to be competitive with your new train, or you will suffer their fate. The competition is transportation, not slow machines on tracks.

“Advantage” needs to be measurable and significant. Many entrepreneurs lead with fuzzy terms like “improved usability” and “lower cost.” Experienced business people realize that unless you are dealing with a commodity, or customers are extremely unhappy, they won’t switch to a new alternative unless the savings are well above 20%.

So what are the business elements that investors look for to conclude that you may indeed have a sustainable competitive advantage? Here are the key ones:

1. Real intellectual property. We can all argue the shortcomings and non-defensibility of patents, but these are still your best competitive protection, sustainable for twenty years. Others of lesser value include trademarks, trade secrets, unique domain names, long-term contracts, and copyrights.
2. A dynamic product line, rather than a single product. If your product or service looks like one-of-a-kind, with no planned follow-up, you have a weak position. The best position is some innovative technology, with a great initial product, and a big list of follow-on products that can be commercialized to keep ahead of competitors.
3. Dramatic cost improvement for cause. What we are looking for here is a breakthrough in technology (patented), manufacturing process, or new revenue model, that results in an order-of-magnitude cost reduction. Saying that you will work harder and more efficiently than competitors to keep costs down is not convincing.
4. Proven team with inside relationships. Great people are always a real competitive advantage. Many markets, like government contracts, are especially costly and time consuming to penetrate, but if your team already has these connections, you have an immediate head start, and past leadership success suggests you can sustain the lead.
5. Lock on the market or customer base. If you already have a brand with a large customer base that is relevant to this new business, that’s a tremendous advantage, and it’s sustainable if you can maintain the momentum through complementary products. Investors will look at turnover rates, cost of acquisition, and revenue streams.
6. Strong focus and differentiation. A new social networking product that proclaims to combine the best of Facebook, MySpace, LinkedIn, and Twitter has too broad a focus and will likely not compete in the long run with existing offerings. Combining functions is not a good differentiator.

Overall, a sustainable competitive advantage requires value-creating products, processes, and services that cannot be matched by competitors now, and plan content to maintain that position as you scale. Of course all of this assumes you are in a big growing market, with adequate resources, marketing, and great people to deliver. No one said it would be easy!