Dig for Diligence

A primer on the venture capital due diligence process

Greg Bergamesco
Risky Business


Image: Shutterstock

One of my favorite movies is Raiders of the Lost Ark. A pivotal plot element in the movie reveals that the Nazis have thousands of men looking for the ark, but digging in the wrong spot. Indiana Jones and his two friends, armed with additional information, find the right spot and uncover the ark (only to have it taken from them, so that we get an additional 45 minutes of a great movie).

One of the keys to being a good venture capital investor is knowing where and how to dig for information. Diligence best practices are crucial to making good investment decisions.

Indiana Jones uses the Staff of Ra to determine the right location to dig for the Lost Ark of the Covenant; venture capitalists use due diligence best practices to dig for insights on potential investments

What is Due Diligence?

Due diligence is the process of digging into a potential investment to learn key details about a company before investing. In the process of meeting with a company, the entrepreneur makes certain representations. Diligence allows a potential investor to determine whether those representations are accurate. The process allows VCs to assess a company’s risks before finalizing an investment decision. During diligence, we attempt to understand the four main types of risk that could derail an investment: market, people, technology, and financing.

Due diligence is sometimes dreaded by entrepreneurs; but if done well, diligence can be beneficial to the startup. Through thoughtful due diligence, a VC will learn the “ins and outs” of a business, and ultimately uncover patterns of success or failure. Good VCs know that sharing both positive and constructive feedback during the diligence process is a way to build trust in their long-term relationships with entrepreneurs.

Here is how Touchdown Ventures approaches due diligence:

First Start Digging: Preliminary Due Diligence

After meeting a company several times, we have formed a thesis for why the investment could be successful, and we have also begun assessing potential risks. This begins a process called preliminary diligence, where we probe into the opportunity with minimal help required from the entrepreneur.

From our initial meetings with the company, we have begun to understand the history of the business, the management team’s backgrounds, key metrics, competitive landscape, customer pipeline, and so on. During preliminary diligence, we start to perform references, including with industry experts, and assess the potential for competitive advantage by understanding what other entrants are attacking the same customer problem.

The goal is to be as objective (and therefore skeptical) as possible and identify potential “yellow flags” that might invalidate our investment thesis. Even the best companies will have potential problems. If we find “red flags,” we typically stop the process and decline the investment. Once we have completed this process and further socialized the investment opportunity internally, we determine whether to move it into full diligence. If we decide to continue, those identified yellow flags become the key focus of our full due diligence. Where preliminary diligence might require 20 hours of work, full due diligence could potentially demand upwards of 200 hours of work from a team of venture capital and legal professionals.

Then Dig Deeper: Full Due Diligence

Entrepreneurs may have experienced or heard about VCs asking for a laundry list of materials to perform full due diligence, but it’s helpful to understand that the primary goals are to validate your story, and pick apart those yellow flags to make sure we are making conscious decisions about the risks we are taking. This also helps us price the investment properly.

Experienced VCs also know entrepreneurs tend to paint the picture that their company is the strongest competitor in the market and has the best product. To remain disciplined, VCs must develop their own market knowledge and network of industry thought-leaders to pull together an objective and sophisticated view of the company’s strengths, weaknesses, opportunities, and threats. Therefore, the full diligence process is far more involved and requires meaningful input from the entrepreneur.

As described above, venture capital diligence focuses on understanding the four main types of risk that would adversely affect an investment. In full due diligence, we dig even deeper into these same issues:

1. Market Risk: We usually speak with three or more customers or potential customers, depending on the stage of the business. These could be customers that the company has shared or references that we know well (“off list” references). Our questions attempt to validate whether the product of service solves a real need, and whether the customer has committed budget to address the problem.

2. People Risk: We also speak to multiple management team references to understand personal and professional strengths and weaknesses. Good “back channel” references can include former employees of the company or people who have worked with the senior management team in their previous companies. We also want to know how the board of directors supports and advises the company. Sophisticated and dedicated Board members often play a key role in a company’s success.

3. Technology Risk: We frequently work with technical experts, who might be corporate executives or a portfolio company CEO or CTO, to validate the startup’s technology, intellectual property, product roadmap, and platform scalability.

4. Financing Risk: We build our own financial projections based on the company’s model, with sensitivities to understand downside cases for the company’s financial outlook, and in particular cash requirements that determine the timing of future financings.

The four main types of venture capital risk

What happens when due diligence goes wrong?

It’s easy to miss risks when due diligence is sloppy or simply not done. We have seen technology architectures which cannot scale due to flawed designs, founders with “skeletons in their closets,” undisclosed or pending lawsuits, and products with fatal market acceptance issues. It’s far better to surface and understand these kinds of issues prior to making an investment.

Venture capital due diligence helps identify weaknesses in a company and understand the entrepreneur’s plan to address them. It can be a tedious process, taking weeks or even months when performed thoroughly. And even when done right, venture capital remains the most risky investment class around, so there will always be “unknown unknowns.” It’s not possible to forecast everything that might go wrong prior to making an investment, but diligence helps make the decision conscious, and not a gamble.

Other Best Practices

Here are some other best practices that we have found can make the process entrepreneur friendly and yield good results. Consistent and honest communication is the foundation for building trust and for developing a good reputation in the venture capital and startup community.

These frameworks can help VCs understand and manage the risks associated with each potential investment.

Due diligence mistakes can be (almost this) costly!

While the downside of making a bad decision isn’t quite so bad as having your face melt, like in Raiders of the Lost Ark, investors can lose a lot of money by being sloppy or negligent during due diligence. If you are interested in learning more about why it’s so important to follow a trusted due diligence process, read Why Due Diligence is Important written by my colleague, Scott Lenet. He shares his insights from a narrowly avoided horror story.

Liked what you read? Click 👏 to help others find this article.

Greg Bergamesco is a Principal of Touchdown Ventures, a Registered Investment Adviser that provides “Venture Capital as a Service” to help corporations launch and manage their investment programs. Touchdown’s Philadelphia-based Director Eric Budin contributed to this article.

Unless otherwise indicated, commentary on this site reflects the personal opinions, viewpoints and analyses of the author and should not be regarded as a description of services provided by Touchdown or its affiliates. The opinions expressed here are for general informational purposes only and are not intended to provide specific advice or recommendations for any individual on any security or advisory service. It is only intended to provide education about the financial industry. The views reflected in the commentary are subject to change at any time without notice. While all information presented, including from independent sources, is believed to be accurate, we make no representation or warranty as to accuracy or completeness. We reserve the right to change any part of these materials without notice and assume no obligation to provide updates. Nothing on this site constitutes investment advice, performance data or a recommendation that any particular security, portfolio of securities, transaction or investment strategy is suitable for any specific person. Investing involves the risk of loss of some or all of an investment. Past performance is no guarantee of future results.



Greg Bergamesco
Risky Business

Venture capitalist at Touchdown Ventures, and proud father of two boys. ND alumnus and fan for life.