My business partner Mickayla and I wrapped up the fundraise for Groove Capital Fund II at the end of May. [Bang the gong]. It’s a $15.5 million fund, which will be used to lead pre-seed rounds in high potential startups located in Minnesota. We’re incredibly blessed and thankful for the people and institutions who chose to partner with us in our goal to find and elevate the area’s next generation of business leaders.

If you talk to any founders or other investors who have been raising money in the last 18 months, you may be aware that it’s been an incredibly challenging fundraising environment. Decisions are moving very slowly, and a lot of the capital is either going to other things or has completely dried up. And though we exceeded our goal for the second raise, I’ll admit that it was exhausting. In the year-and-a-half that it took to pull it together, there were times of joy, frustration, desperation, hope, and growth. It was a real rollercoaster.

Lessons were learned and tools were sharpened; the experience leaves you with a better appreciation for your fellow entrepreneurs who are raising funds themselves. In respect to those founders, we share what worked for us. Hopefully something here can help you unlock your own fundraising efforts.

Having Goals Will Help You Focus

To start, raising money is a sales job. It’s impossible to raise cash if you don’t like sales and if you don’t believe in what you are selling. If you are uncomfortable with asking for money (which is normal), you may find yourself putting other tasks ahead of your fundraise, and before you know it another week has passed without any progress. Sound familiar?

This happened to me last summer. We jumped out of the gates fast thanks to a number of our Fund 1 investors recommitting to another partnership. But shortly after our first close, our raise got stuck at about $9M for three months. We can blame a banking crisis, war, inflation, etc., but the reality is that I took my foot off the gas and did not prioritize a core responsibility—closing the fund.

Going into Q4, I set out a goal to have 50 meetings before the end of the year. I was probably pretty close to that number in previous quarters, but the fact that I don’t know illustrates that I didn’t have a clear set of goals for myself. I finished Q4 having completed 64 meetings, while adding another $2 million to $3 million to our running total. In Q1, I completed another 54 meetings, and got the fund in the position we needed to exceed our goal of $15 million.

Find People Who Share Your Values

If the idea of having 100 meetings makes you shudder, here’s another hack: Meet with people you want to spend time with.

Comparing our first raise to the second, a major shift that occurred is that we spent a lot less time trying to convince people and a lot more time talking about purpose and values. We’re still selling an asset, and so there has to be a shared understanding that generating a compelling return is the primary objective, but once that box is checked, we found ourselves in more meaningful conversations about things like legacy, and the good that others were looking to create for themselves and their community.

Not every meeting ended with an investment, but nearly all of them that included sincere conversations around motivations, goals, aspirations, and other higher order topics usually did. Those conversations were important, meaningful, and fun.

Take the In-Person Meeting, if it’s Offered

Investment decisions are based on trust, and trust is difficult to establish without time together. It takes more time, costs money, and is more complicated to meet people in person, but it is worth the investment.

Around tax time, I was calculating the miles driven to the various meetings that occurred in 2023. Adding it all up, I had driven the equivalent of a trip to Houston and back. Looking at the receipts from the meetings, we easily spent hundreds of dollars buying coffees and lunches (major shoutout to Yum!, FRGMT, Nolo’s, The Hilltop, Cafe Ceres, and the rest of investor-meeting hotspots).

When others may have relied on something virtual, we defaulted to in-person meetings, and it worked.

Ask for Help

I have a distinct memory of a time in January when I was looking at my sheet of unfilled meetings and was paralyzed wondering who I could possibly meet with to reach my goal of another 50 meetings by the end of the quarter. We had already exhausted all of our personal connections; everyone was either in or had politely passed. The leads were weak.

Then something magic happened.

We got super intentional about asking for help from existing investors and portfolio companies. Our broadcast for support was immediately followed by direct outreach with very clear instructions on who we were looking to meet with and why. It was a little uncomfortable and felt like we were creating a burden for the partners we cared so much about, but we were pleasantly surprised to see a near immediate response by both groups to open their networks. Their advocacy not only expanded our network of potential partners, but their introductions came with context about the positive experience they’ve had working with Groove (the real Glengarry leads).

We’re incredibly grateful for our community’s willingness to lean in and support our efforts. It’s a good reminder of the importance of taking care of your people and asking for help when you need it.

Do What You Say You’re Going to Do

Your follow-through will make or break your fundraise. Towards the end of every meeting, I made a very concerted effort to call out the items that I was committing myself to as a follow-up. This act serves a few purposes. The first is that it demonstrates that you were paying attention to the conversation. People appreciate knowing that you were listening to their questions and keeping track of the things that may require additional information.

Your follow-up also is a great way to provide information that you may not have had the time to cover during the conversation. The items you include in an email give you a perfect opportunity to show how prepared you are and how much time you’ve put into whatever project you are looking to raise money for.

Lastly, saying that you will do something and then doing that thing builds trust. While most other people fail to close the loop, you follow through and show from the very beginning of the relationship that you can be trusted to do what you say you are going to do.

I wish there was one thing to raise a million bucks or three simple hacks to raise in three weeks, but that’s not how it works. However, the tools and practices that you can implement today to speed up your fundraise are very basic: focus, set goals, create meaningful connections, be yourself, believe in your vision, share your story, stay positive, and close the loop. You got this.