Scale Up

How to Select an Investor in 2023

Nikki Parker, Ryan Hinkle / January 31, 2023
pass the baton

Preparing to raise capital in 2023 might feel daunting given the market, but it doesn’t need to be. For great businesses, there are investors (like Insight) who are ready to invest.

Before thinking about raising money, we’re going to assume founders have checked off some of the basics listed below:

  1. Know your specific business needs for the investment. This should be deeper than the amount of money you need to raise. Founders/CEOs seeking funding should have a well-defined business plan that outlines company growth goals, target market, financial projections, and competitive advantage. This helps articulate the value of your business to potential investors and demonstrates an understanding of the industry and market.
  2. Prepare your leadership team. Fundraising takes time away from running the business, which means your leadership team must have the skills, experience, and dedication to execute the business plan and drive the company’s growth. Assemble a team that has a diverse range of skills and expertise needed to achieve the company’s goals.
  3. Have a clear plan for using the funding. Investors want to see a clear plan for how the new funding will be used to drive the company’s growth and generate a return on investment. Be prepared to present a realistic, detailed plan for how the investment will be used to achieve specific milestones and grow the business.
  4. Finally, map the market of potential investors. Asking other entrepreneurs for advice and introductions is a great way to start the fundraising process.

Once these steps are done, you’re ready to begin seriously contemplating your next fundraising partner. Deciding to bring someone new onto your cap table can significantly strengthen your business for the years ahead and inject the capital needed to move from a startup to a scaleup.

Some tips for founders:

Prenup discussions on the second date.

Being prepared with your goals and expectations for raising capital is great, but in today’s market, it’s important to have an open mind and willingness to have a conversation. In the negotiation of final documents, there is always a clear set of rights regarding rules of engagement if things go right — and if things go wrong. While this can feel as off-putting as discussing a prenuptial agreement early in a relationship, it is important all sides understand rights and agreements for all scenarios. Consider your position if things go wrong. What happens when things go wrong is as important as the conditions when things go right.

Consider dilution in addition to valuation.

You’re obviously seeking out capital, but don’t simply fixate on your company’s valuation number or the specific amount of money you want to raise. The more important consideration in the long run will be understanding the percentage of the cap table you are hoping to raise. While value is always important, if you are only raising primary capital you should consider dilution more than the post-money value. For example, if you are hoping to raise $25M at a $125M post (20% dilution), you can offset a 25% price disappointment by lowering the amount of capital raised. You can raise at $80M while limiting the raise to $20M. This is also 20% dilution. The only difference between the two deal structures is $5M on your balance sheet. The point? Valuation matters, obviously. But it’s only one of the variables. You can control the impact of valuation by adjusting the investment amount.

You want a partner that has enough capital to ideally support you through your next few rounds, and ultimately, deliver enough value to scale your business in meaningful ways beyond a sky-high valuation or fundraising amount.

Have conviction in what a new investor can do to add value.

This means two things. Firstly, what does the investor’s investment horizon look like? Do they have the capital and patience to be able to support you long-term? Secondly, how will the investor work with you and your team? It’s critical to know the skillset of your lead investor and ensure that they understand your industry, business, and goals for the years to come.

Besides the financial support of your investor, different firms will have different levels of deeper support available. At Insight, for example, there is a large team set up to support each individual portfolio company, streamlined through a portfolio management function. This ensures impactful, personalized support is delivered when and where it is needed most for each portfolio company.

Most CEOs and founders who choose to work with Insight are particularly excited by having access to Insight Onsite, a team of more than 130 of the software industry’s best operators, dedicated to supporting portfolio companies as they scale up. Understanding what resources different investors have available to you will help you strategically map out your board and partners to best support you at your stage of growth.

Select an investor with a network you can leverage through your journey.

Investors can be incredibly valuable partners and bring a unique perspective to the boardroom. However, being a CEO (or another C-Suite role) at a growing business in today’s climate can be an intimidating and lonely job. Insight’s portfolio of 600+ companies provides CEOs with an unparalleled peer network to lean on and learn from. Having a pool of people who are in your shoes and navigating the same challenges can be one of the most transformational assets for CEOs when building their business.

Insight’s portfolio experience programming is one of the most robust in the industry, made possible because of the global breadth of the portfolio. In 2022 alone, executives accessed nearly 80 intimate digital roundtables and webinars, and over 30 in-person events. Many of Insight’s CEOs choose to participate in the MINDSET CEO Summits, where, alongside their peers, they’re able to dive deep into the leadership and operational challenges they’re facing today and walk away with trusted advice on what to do next. Insight’s portfolio events are all designed to forge strategic connections and actionable tactics.

Raising money can be a challenging process, especially in 2023. But prepared with the proper guidance and expectations, finding the right partner can be transformational to the future of your business.