How to protect yourself from bad investors

What to look for, what to avoid and how to due to diligence Startup investors

July 24, 2020

How to protect yourself from bad investors

Many first-time founders have grand dreams that only some money can make a reality. To achieve it, they set their goals by their success in fundraising, and they are happy with any type of money raised in any form. They go about the entrepreneurial ecosystem impressed by check sizes their peers raised and believe this is an excellent metric for success.

This mindset exposes founders to taking money that can harm their journey.

In this blog, I'll review what to look for in investors and what to avoid. Hopefully, finding the right investor will enable you to build a strong partnership with those investors that will lead you to success and generate significant returns for them.

If too busy or just can't be bothered - scroll to the TL;DR section.

To begin with, why is your startup fundraising?

Let's start with the trivial motivation for you being in the market, looking for money.

Even if you and your team are all on Raman now, history shows it won't last forever. You will all need salaries to eat and live, but moreover, the company will need money to move forward.

The most efficient planning of your ideas testing scheme will require some money to test them out. Without money, you are always stuck in the "chicken and the egg" scenario: I can' test and develop my ideas if I don't have money. I won't have any money until I have some proof of my thoughts. You can always bootstrap some parts. You should always be as intelligent and frugal in managing your efforts, but keep in mind that time is always of the essence, so using money to move faster is not only logical but many times smarter. With that understanding in place, you can plan how much money you need and how you plan to use it. The most important part is what would be the next step if your plan succeeds. Will you raise another round of funding? If so, from who and how much? If not, will you use the cash generated from revenues to drive growth?

What are the startup investors' motivations, and what do angel investors look for in a startup?

A simple viewpoint will assume investors invest in making money or generating favorable returns.

While that is always the case, this answer is very lacking. Many angel investors are actively looking to help entrepreneurs as part of their ideology. They might view it as their social responsibility to provide capital to young companies and guidance and support.

Others might view startup investment as an asset class for diversification. Some corporate invest in startups using their corporate VCs to keep their fingers with the pulse in the industry, rather than relying on analysts and 3rd party reports.

Setting investor vs. founder expectations

Many founders are pitching like car dealers. Life is seen through pink glasses, and the future is rosy. That is all well as an initial hook, but it's best to have an honest discussion about what each side expects in the long run and why they make the investment.

Some investors love to be involved; others are looking for a passive investment. Some expect their investment to be paid in full with some excellent return in the next round of funding. Others plan to go "the full monty." Some investors expect the company to stick to its "vision," while others expect it to pivot, often searching for a business model. Some investors are happy with a small exit, while others will consider nothing but a NASDAQ IPO.

These differences in expectations will create differences in strategic thinking, which will lead to tension. Sometimes this tension can be mitigated, and sometimes it may cause the founder and CEO to be ousted. In general - the company's CEO is perceived as the one who knows the company and industry best and will set the tone. Losing the faith of the investors may cause the loss of the CEO title. Here are some examples:

  • It's best to list in advance each sides thoughts about the near future as well as the vision
  • Does the company aim for IPO/M&A/evergreen?
  • How fast should the company recruit and grow the team?
  • Which function do we grow at a priority? Sales? Marketing? Product and engineering?
  • What does an expected budget look like for the company? E.g., Many early-stage investors are surprised the founder is expecting a salary after two years of bootstrapping.
  • How is the company expected to grow?
  • At what level of "days to live" do we start to fundraise?
  • What level of involvement does the investor have? In what capacity? Is there compensation as part of that expectation going to the investor?

Industry knowledge

Industry experts provide information on industry benchmarks and connect with vendors, partners, and distribution channels. They can give feedback on the progress as well as help to set the right goals. All these make an investor who comes with a strong industry experience worth more than their dollar investment. Many investors will claim they have expertise in the industry to sell their value, and since some expertise in one sector has some carry over to another, this is true in the board sense. Having said that, the further the distance between the industries, the less likely that advice will be applicable in all cases.

When evaluating how helpful the investor will be, try to assess the similarities and differences in his experience. Example of items to look for:

  • Industry - the more specific, the better.
    For example, "this investor is great for us as they have B2B experience" is much too broad. A much better fit would be "we are a company that develops quality control solutions for the metal manufacturer, and this investor was the head of biz dev for a public company selling to quality managers in manufacturers."
  • Size of company - If the investor is inexperienced with large corporates, much of his advice will be hard to implement. "You want market awareness. Get the biggest booth in the show."
  • Business model
  • Company stage - if they've never been involved with a company that has not fully proved their product-market fit - they would not even know what the search process looks like.
  • Company funding background and vision
  • Company long term goals

Value add

Every investor will claim they have a lot of value add that exceeds their check size. This claim is easy to make but very hard to prove or validate. Some large investment firms not only talk the talk.

Traditional investors were focused on investing their own money or money they have raised for their fund. The primary role of the investor was to achieve superior returns by deploying cash to the best opportunities in the market. Sure, they took board seats and gave valuable advice when needed, but this is it.

Andreessen-Horowitz was the first VC that changed that model. It was started in 2009; this fund actively works for its portfolio companies by providing them with high-quality services such as recruiting, digital marketing, branding, training, and more. Many VCs claim to follow the model, but very few do. A VC might show a public relations person as part of the team, but the only PRs that person will ever actively drive are related to the fund itself, giving you no value whatsoever.

Operational experience

Many investors would claim they can bring value to you via "operational expertise." That is true, but it's best to understand what that means and set the expectations between the parties going forward.

When the founder hears the investor brags about operational expertise, it is essential to understand how relevant it is to your company. First, go through the same questions as reviewed in the industry expert section. Then try to understand which organizational function these investors are most experienced with and whether it fits your needs. Were they headhunters in your industry or chief marketing officers? Did they manage the sales organization or made the first sales for a startup. If they were CEOs, they'd bring the broadest viewpoint but also the least function-specific expertise.

The last thing is to understand the expected level of involvement you should expect from that investor and if it comes with additional cost. The founder might expect an ongoing heavy engagement while the investor is OK with a short advice phone call once every couple of weeks.

Some people say that if the investor expects the company to pay them anything for their services, it's a bad sign. I do not hold this position but rather the opposite. In my humble opinion, if the investment is substantial compared with the services provided, it's a good thing. For example, an angle that invests $50K in a company and has a marketing agency that offers hourly training for $100/hr. If they sell the company a full day of training every week, it will take the investor more than a year to "recover" their investment, suggesting the structure was not set to drink all the funds in the company using a straw.

In these cases, it is helpful to limit the paid engagement in advance to a limited project or timeframe. This limited engagement would allow a softer "breakup" if the company doesn't need the services any longer or chooses a different vendor.

“Money does not smell”, or does it?

Many entrepreneurs, especially in the early stages, are happy to raise any money from any source. In the long run, this can prove to be problematic. First of all, in the US and other countries, the selling party (e.g., a startup raising A round) is responsible for ensuring all investors are accredited or handle the exceptions. But even if all your investors are accredited, it doesn't mean it's a match made in heaven.

Different investors have different expectations - about the level of involvement in the company, how quickly they should see a return, how volatile the business is, and the capital requirement for a business in this industry. Dreams of huge exits woo many inexperienced angels. They may invest in pre-seed dreaming of unicorns. However, in later rounds, they are surprised by how much capital is needed to feed a unicorn. They will be diluted, they will lose their rights, and in some vicious cases, they might be exposed to a "pay-to-play" scenario where they will be diluted faster than expected. All these will create tension between the founder and those investors that can derail into a legal conflict.

To avoid all these, make sure the investor you bring on board either has a lot of experience in the specific field, or you help them understand what is expected, even at the risk of losing the investment. For example, an investor in the restaurant business may be OK with the initial investment check, but they might expect a hefty dividend after the 3rd year. Since tech startups seldom pay dividends before they IPO, this is a tension point that needs to be cleared out before the partnership is signed.

Non-democratic countries

Some investors might "block" future investment. For example, they raise money from investors whose money source is shady or investors from non-democratic countries. While it's not "fair," some non-democratic countries are getting waived as “its OK to take their money”, while others will paint your company as untouchable. In doubt, it's best to avoid even seemingly legitimate sources of funding if those risk is pushing away institutional investors down the road.

Future round participation 

It is also essential to understand what sort of monetary (money) support this investor is expected to provide down the line. Will they participate in follow-on rounds?

Many angel investors are active in the pre-seed and seed stages but do not keep their pro-rata in more advanced rounds, which is expected. However, if a VC participated in a previous round and would not participate in future rounds - it sends a terrible signal, regardless if this is a small VC.

Monetary support in hard times

What happens if you fail to raise a round and strapped on cash? Will they bridge you until you are in a better position? How easy is it for them to make that decision? Is it a decision they can make on their own, or is there a committee and process they are bound by (in the case of many corporate VC's for example?

Avoid the Hans Westergaard startup investor

Princess Anna gets to waltz with Hans, a handsome foreign prince she recently met during her sister's crowning. The dance leads to an entire date that lasts the whole night. The conversation flows, the night is beautiful, and the couple seems so compatible. Hans works up the courage to propose, and Anna immediately agrees. A beautiful love story begins.

Well, not exactly. The queen objects to the whole thing, warning her sister it's an awful call to marry a stranger she just met, but Anna doesn't heed her sister's warnings.

Fast forward some 30 minutes, and prince Hans is revealed to be a power-thirsty psychopath that not only cares little about Anna but is willing to sacrifice her to achieve his goals. Bad prince Hans.

While Disney's Frozen depicts the dangers of fast-moving relationships using songs and magic, you won't feel so magical if you brought in Hans as your investor. Below we'll list some examples you should avoid.

Toxic people

The board of directors' role is to set the company's strategy and to overlook its activities. If things are not going well, they should suggest and even force changes to executive management. But some investors hold a playbook the founder is not aware of, and when the time comes, they will try to execute their plan. While this is more related to what strategy an investor believes will grant the best return for their money, there is also a personality issue.

You might have strong disagreements on strategic items with some investors but strong cooperation in executing an agreed-upon strategy (by the board majority or simply accepting one viewpoint for a test period).

However, investors are people, and some have toxic personalities which can be deadly to your company. A toxic investor might turn other investors against you, wearing down the company using legal tactics, giving bad PR, etc.

Trying to figure out personality fit is probably the hardest to learn about in advance because people don't tend to wash their dirty laundry in public. Still, you should certainly try to get an understanding of the person you'll be working with.

Prioritizing their interests above those of the startup or the founders

An example easiest describes this case:

A company raises seed-round funding from a micro-VC and manages to hit cash flow positive with the raised money and its sales. The company decides to improve its current processes to provide a better customer experience and is planning to raise another round of funding in a year, once it can show even more organic tracktion and get much better terms and attract better investors. As long as the management and board believe it's the best strategy, there is no reason to question it in everyday operations.

However, if the micro-VC is in the fundraising mode of a new fund during that said period, it cares to show short-term changes to its investors. As such, it may push the company to a less-than-optimized up-round, just to expose the hidden value created by the company in its internal IRR reports. Most often than not, this motivation will be masked by arguments such as "we should grow faster," "raise money when you can, not when you need," "rumors talk about a blackout period in investment. Rush to get money today."

The critical takeaway here is that while the investors want the company to succeed, some might care for their success even more. As they may be active in many companies - pushing one company to do the right thing for the investor at the company's expense.

Driving your startup off the cliff

This point is more focused on VC investors, and to understand this point, one must understand how VC's make money and how they operate, which is out of the scope of this blog. I'll just say this: contrary to the intuition, even in the most successful VCs, most VC's investments fail, and this is by design.

A startup taking VC money has to adopt the mentality of "go big or go home," but founders usually have one company. The founder's economic future is typically tied to the success of this single company.

This economic gap creates tension between the founders and the executive team's appetite for risk compared with a VC investor. In most scenarios, the VC in the board of directors will push for the most aggressive, riskiest, moonshot strategies. This aggressiveness isn't derived from their love of risk. Instead, it is derived from the diversification of risk across many companies. Moreover, if the company runs out of cash, the VC can choose to "bail" it, probably being very strong at the negotiation table facing the founders and the other inventors.

Having an aggressive member on the board is not a bad thing in itself, but it is terrible if there is a misalignment between the executive team and the board and or between the board members themselves.

Invest in a sector - including investing in competitors

Most investors would have focus areas that reflect both their experience and forecasted opportunities in the market. These investors might try to invest in many early-stage companies in a specific industry, hoping to hit a winner.

The problem is that many of these companies will have overlaps on day one, and they might also pivot to step on each other toes in the future. The "industry investor" can try to sway a company from moving into the territory of one of his more significant investments. It can also pass general industry information to competitors, e.g., "this and this trade shows don't provide good ROI." If the information streams in all directions, this might be a good thing. The problem is that the only party controlling the information stream is the investor, and as time goes by, streams can change direction.

To avoid this, see how the investors behaved to date.

Did they invest in indirect competitors? Did they get out of an investment if one of their companies "moved" to the territory of the other? How do they react when highlighting this problem?

Have a history of “educational” meetings or copycating

Many first-time entrepreneurs are anxious to talk about their new startup idea since they are concerned it will be copied. This concern makes them wonder about the best way to get investors to sign an NDA before a meeting. The reality is that professional investors don't sign an NDA for many reasons. Most of the reasons are legitimate, such as they had already invested in a similar idea before meeting you, so they don't want to expose their company to a lawsuit. But the custom of allowing investors not to sign NDA's also allowed them two bad practices:

  • Educational sessions
    In this case, the investor might be interested in a new field. They might even have already signed a TS with a company in the area, but before the investment goes public, they would invite other companies in the field to pitch their idea with no genuine intention to invest. They only care to get information and get educated.
    This practice not only wastes valuable time of startup founders for a one-sided benefit other than their own but might also actually hurt the founder. If the "educated investor" invests in any competitor, some information might be precious down the line, such as GTM strategies tested, marketing channels, distribution partners, and more.
    One would argue you should hold your cards close to your chest, but the reality is that you want investors to be engaged while you are meeting them, asking many questions, and trying to understand as much of the business as possible. It's tough to tell if they like your company or they like the information you provide them with only to use it in "their" company."
    This tactic is brutal to defend against, but culprits of this behavior tend to repeat it as they find it fair play. Just ask around in your ecosystem if anyone was experienced any educational sessions.
  • Copying your idea
    Up until 2020, I would say anyone that is concerned with anyone copying their ideas is just too new to entrepreneurship. But 2020, being the fun year that it is, showed us that bad could be worse. In this article by the WSJ, Amazon's VC supposedly met with startups only to launch a competing product. I'm not sure what is the best defense for these tactics, but if you are doing anything in such VC realm, better to stay away from them.

Cultural differences and the executed term sheet negotiators

A standard VC deal will usually have a significant milestone which is signing a term sheet. The term sheet states the principal commercial terms, puts the startup on "no-shop" for 30-60 days, and allows the investor to invest more in legal and financial due diligence. Good investors will push for the closing of the deal ASAP.

However, some investors would delay their progress to the end of the no-shop period, knowing the founder position is weakened as time goes by due to lack of money and for not reaching new investors in the no-shop period. When this time comes, they'll negotiate the basic terms of the deal even if the new terms contradict those stated in the term sheet. This strategy is an acceptable business practice in Asia but will result in a culture clash when the investment in question is made in the US.

When doing your due diligence process, make sure to query how "distant" were the closed deals from the term sheet. If many new terms were introduced in the closing phase, or the commercial terms were changed in between, consider if this potential deal is worth the risk of entering a no-shop period.

Even if a deal is closed, cultural differences may make the partnership hard down the line. Ensure that the investor has the needed flexibility, and you can deal with these differences without them taking too much of your focus. A way to somewhat mitigate this is to accept investment by foreign investors but minimize their influence, such as refusing board seats or any extreme veto rights. It is possible that without those, you won't be able to close the deal, but quite possibly, with those, you'll enter a long-term board clash that might not be possible to fix.

How to avoid the wrong investor? Do your due diligence on potential investors

Just like investors run a due diligence process to avoid the wrong investment, the founder should run a due diligence process to avoid the wrong investors.

Before reaching out to an investor, try to understand how well they fit your company. We’ve given some background here.

You should do some secondary research which should include:

  • Their LinkedIn profile and experience
  • Their Crunchbase profile and activity
  • Twitter activity
  • Professional groups activity
  • The media mentions either of them or companies they are involved with.
  • Media mentions for founders who picked up investments from them.

If you decide this is a good start, engage with the investor and pitch them the investment opportunity. Naturally, this is the most challenging part and with a relatively low expected probability of getting a yes—a simple fact of life.

If the investor is showing interest in investing, it's best to have some primary research before going into any binding commitment.

Interview the investor and try to both get as much information as well as set the right expectations.

Then try to get a reference call with founders who took investments to form that same investor.

If possible, you should aim to interview founders from different periods, as well as try to get an interview with whoever was:

  • First-time founders at the time of the investment
  • Founders which companies have failed while having the investor engaged
  • Founders that companies have exited while having the investor engaged.

The reason for both of the last is that both extreme scenarios introduce a lot of tension to the investors-founders discussion, and they provide the best indicators to how the investor would behave in rough times. If you get the slightest aversion to taking that investor's money, you should dig deeper before you make the call. In addition, it is good to try and get the perspective of other investors that shared the table with the potential investor on past deals. Get indications of how helpful they were, how they behaved in board meetings, and how much value they added.


Due diligence investors thoroughly before taking their money

Try to find:

Real value ads

Real operational expertise in fields you are lacking


Shady money sources

Toxic personalities

Clear history of conflict of interest

Clear history of driving the company over a cliff

Unfair practices

The ambiguous expectation on cash flow

The vague expectation on involvement


Some first-time founders will dismiss the above because these are "high-class problems." First, you need to survive, so raising any sort of money is better than not raising it at all. While I get this position, I would argue that is not the case and would urge them to consult more experienced entrepreneurs before taking toxic money.

Startup life is hard, to begin with, and the odds are against you. If you take the wrong money from the wrong investors, you'll be stuck in a bad relationship for a long time. What's more, your probability of succeeding will practically become nonexistent. It's better to spend more time on your business, improve it in every aspect and make it more attractive to suitable investors. It's also better to spend more time finding the right investors.

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