Why Investors With an Entrepreneurial Past are Vital to Startup Success

In this article, I would like to focus on one significant trait that some investors possess — an entrepreneurial background that enables them to establish strong connections with startups and better understand the ‘pains’ and challenges new founders face.

Based on my personal experience as an entrepreneur I would like to highlight key aspects of communication with startups and why your entrepreneurial past makes you a little bit different from others.

Related: 6 Steps to Finding the Right Investors for Your Business

Speaking the same entrepreneurial language

When communicating with founders, having an entrepreneurial background is extremely helpful. Founders can sense it, even from how questions are formulated, and they often highlight they have never been asked such questions before — questions are tailored with a deep understanding of the subject.

And it’s not just about technology-related topics, but specifically business management, such as sales funnels, marketing strategies, product market fit and customer development. Besides managing businesses, having personal experience in creating acceleration programs and all the leading methodologies of Silicon Valley, which we have integrated into accelerators for many years to make them more effective, can enhance communication between investors and founders.

With my experience of establishing 42 accelerators and collaborating with 1500 alumni startups, I have encountered familiar patterns, challenges and intricate situations when working with founders. We have found solutions together with startups in the past, and now I bring that experience to my current communication with founders.

Entrepreneurs then — investors now

Investors with entrepreneurial backgrounds bring valuable insights and expertise to the table. They have firsthand experience navigating the challenges and uncertainties of building a business, which allows them better to understand the struggles and aspirations of startup founders. Here are some great examples from the venture world.

Mark Suster is a well-known voice in the investing world, having written extensively about investing in startups and building them on his website, Both Sides of the Table. He possesses the unique ability to discuss both sides of the table due to his experience as a two-time entrepreneur, having sold a company to a French firm and another to Salesforce. Currently, he serves as a partner at Upfront Ventures in Southern California (SoCal).

Marc Andreesen, viewed as a pioneer in the tech space, founded Netscape, Opsware, Ning, and now his investment firm, Andreessen Horowitz. He’s an expert in tech trends and a frequent speaker in the angel investing space.

Reid Hoffman is one of the most sought-after opinion makers in Silicon Valley. He is widely recognized for founding the largest business social network in the world, LinkedIn. Moreover, he has successfully translated his entrepreneurial acumen into profitable investments, with key stakes in companies like Facebook, Airbnb, and PayPal.

Related: 5 Questions to Prepare for Ahead of Your Meeting With Investors

Benefiting from an entrepreneurial past: from coaching to strategic planning

An investor with entrepreneurial skills can provide valuable support and guidance to a startup in several ways. Here are some ways in which such an investor can help:

• Fundraising strategy. The primary role of an investor is to provide funding to the startup and help them with fundraising strategy going forward. This financial support is crucial for the startup to develop its products or services, hire talented employees and scale its operations. With their entrepreneurial experience, the investor can assess the startup’s financial needs and give some strategic advice on funding allocation. Additionally, can guide the founder towards better fundraising strategy and preparation for investor meetings.
• Strategic planning. An investor with entrepreneurial skills can help the startup create a solid business plan and set strategic goals. They can provide insights and expertise gained from their own entrepreneurial background, helping the startup identify potential challenges and opportunities. Together with the startup’s founders, they can develop a roadmap for growth and devise strategies to overcome possible challenges.
• Shared perspective. I think this is one of the most important ways of communication, and here is why. An investor with an entrepreneurial background can better understand startups’ challenges and opportunities. They have likely experienced similar struggles, such as fundraising, market-entry, scaling and operational issues. This shared perspective helps establish rapport and empathy with startup founders, fostering better communication and mutual understanding.
• Mentoring and coaching. Startups often appreciate investors who can go beyond providing capital and act as mentors or coaches. An investor with an entrepreneurial background is well-suited to fulfill this role. They can offer guidance on overcoming challenges, making critical business decisions and navigating the ups and downs of entrepreneurship. Their ability to draw upon personal experiences can be particularly impactful in helping startups succeed.

I love seeing founders passionate about their startups, and our fund sometimes goes the extra mile to advise startups, even if they didn’t receive investments from us. It’s important to remember that when rejecting a startup, there is always the possibility that it may return in the future after making significant improvements in key metrics. Therefore, it is in our best interest to provide additional advice on what steps they need to take to attract funding.

I receive requests from founders for personal consultations quite often. We were thinking about how to turn this demand into something beneficial for startups and society and came up with a very good solution. We decided to combine venture and charity by launching a project with the Podari.Life charity fund called “30 min/lunch with VC to save lives.”

Relationship building

Investors with an entrepreneurial past can leverage their extensive network and connections to open doors, make introductions and facilitate strategic partnerships for the startups they work with. This network can be instrumental in helping startups access resources, industry expertise and potential customers.

For example, the CEO of one of our portfolio companies, PicUp, recently embarked on his first visit to the USA. He took the initiative to go on an extensive tour, visiting key states and connecting with potential partners and investors. I understand firsthand how challenging it can be to establish new connections in a foreign country, especially in the USA and particularly in Silicon Valley, which has no analogs in the world. With this in mind, we decided to assist by connecting the company with investors and key players in the Silicon Valley innovation ecosystem in advance.

Related: The Things Successful Leaders Do and Don’t Do to Build Relationships

What matters the most

In summary, it is not solely the investors’ entrepreneurial experience that founders find appealing. Rather, their experience in different roles inside a business allows investors to have a wider view and help early founders avoid common mistakes while building the next big thing. After all, venture investment is a long-term relationship, and you want to build partner-like relationships with people you will most likely work with for the next 8-10 years until your exit.