Raising funding for your startup can be incredibly stressful. Venture capital firms and angel investors often want to see skyrocketing financial projections with little risk before taking a chance on a tech company. And once you become partners, you’re on business journey that requires an expansive amount of time and energy.
We caught up with a few Boston-based entrepreneurs who recently went through the process to find out the lessons they learned while raising their most recent round of funding.
Raised $11M Series B in July 2016, led by Bain Capital Ventures
Rory Crawford, BevSpot Co-Founder & CEO 
What was the most important lesson you learned while raising your recent round of funding?
Your existing investors are extremely important. To have world-class existing investors when leading your next round of funding is a great signal and very powerful.
Was there a moment where this lesson clicked for you?
During my first fundraising experience. After getting the first strong commitment from a great investor, the process got much easier.
What was the most challenging aspect of raising a round of funding?
Controlling timing and minimizing the distraction from executing on the business. (i.e. fundraising as fast as possible).
How did you combat that?
By doing much of the work up front with the existing investors, ensuring that the process was run as efficiently as possible.
Any advice you'd give to other startups raising funding?
Take money from great investors. They will support you in many ways over time with experience and capital.
How do you think this round of funding will impact the company in the long-term?
It will enable us to accelerate our learning process and shorten how long it will take to get to the next stage.
Raised $3.5M Series A in September 2016, led by Bessemer Venture Partners
Eric Horndahl, Renoviso CEO & Co-Founder 
What was the most important lesson you learned while raising your recent round of funding?
The importance of really crisp storytelling, all the way from the initial intro messaging through the pitch deck. The bar is so high, particularly for the Series A round, that it's absolutely critical to tell a really tight story supported by strong metrics that effectively show the business's early traction and how you will inevitably become dominant.
Was there a moment where this lesson clicked for you?
We did a few practice rounds with the partners at our lead seed investor (NextView Ventures) and it was clear to me that the expectations were going to be much higher for a Series A pitch. The feedback we received on our pitch deck and delivery from our seed investors prior to pitching our Series A targets was invaluable.
What was the most challenging aspect of raising a round of funding? How did you combat that?
While there certainly are some commonalities, each investor that you're pitching is going to focus on different aspects of the business and it's important to read your audience and adjust your pitch accordingly. Know the materials and messaging cold so that you can easily adjust on the fly. One way to combat this is to beef up and leverage your appendix slides so you can go deeper on the areas that matter most for that particular investor.
Any advice you'd give to other startups raising funding?
Given how few deals partners at Series A firms do on an annual basis, it's critical to ensure you're targeting the right partners, not just the right firms. The more intelligence you can gather in order to successfully do that, the better. Partners who have invested in successful businesses where there's some applicability to your business model are more likely to be true believers in your business.
How do you think this round of funding will impact the company in the long-term?
This funding round enables us to build on our strong momentum in order to accelerate growth. We will invest the new funds into our technology platform to further differentiate the customer experience as well as expand into new product categories and geographic markets. And, of course, we're thrilled to partner with a world renowned VC firm like Bessemer who will help us achieve our ambitious goals beyond just the investment.
Raised $3.25M seed in July 2016, led by NextView Ventures
Blair Baldwin, Quilt Co-founder and CEO 
What was the most important lesson you learned while raising your recent round of funding?
For early stage startups like Quilt, focus on the investors or firms that are right for you at your stage. These sources of capital may not be the firms or investors with the largest checkbook or biggest brand, but they are probably the ones who are going to fund your early stage business. It was easy for us to get distracted by interest from large, well-known funds that typically lead Series A rounds. This interest — which was really more about building a relationship for future funding events — diverted our attention from focusing on seed stage funds that were better suited for our round.
Was there a moment where this lesson clicked for you?
After a few weeks of meeting with large, well-known Series A firms, it became clear that our efforts were best spent on cultivating relationships with seed stage funds. Once we shifted focus, we were able to close our round fairly quickly.
What was the most challenging aspect of raising a round of funding?
A wise VC once told me, “Fundraising is all about finding the true believers, not trying to convince the skeptics.” It takes a lot of meetings and pitch sessions to find true believers.
How did you combat that?
Fundraising is much like sales — you need a big funnel to start with and a process to move prospects through the various stages.
Any advice you'd give to other startups raising funding?
Focus on finding an anchor investor / champion first, then build momentum as quickly as possible. Time kills all deals, so once you have momentum going, don't lose it!
How do you think this round of funding will impact the company in the long-term?
Our last round gives us what we need to hit our next series of milestones, including our next financing event.
Raised $2.3M seed in June 2016 led by Accomplice
William Collis, Gamer Sensei co-founder 
What was the most important lesson you learned while raising your recent round of funding?
When pitching investors, your team matters as much - if not more - than your idea. Even the most original concepts have probably been pitched before. And even if an idea is totally unique, executing that idea still matters more. The most critical thing you can do as a startup is make sure you have truly top tier talent on board. It will make funding — and growing your business — that much easier.
Was there a moment where this lesson clicked for you?
When Gamer Sensei found our CTO. As soon as we had an amazing and insightful tech lead, everything got easier for us in our funding quest. We had programmers before; that wasn't the issue. But having the right talent to lead them unlocked our funding runway. This is just an example, but highlights the value of having the right team for your dream.
What was the most challenging aspect of raising a round of funding?
The biggest challenge Gamer Sensei faced raising our recent round of funding was creating urgency. Particularly when entering a completely new space as Gamer Sensei did with eSports coaching. It was easy to get initial interest but harder to push investors over the line.
How did you combat that?
We looked for investors who truly understood our space and our vision. When pitching, it can feel like there are thousands of potential funding sources and always another, fresh pitch to begin. At Gamer Sensei, we focused on identifying high value investor who truly and deeply knew the eSports space and appreciated our vision. This made it a lot easier to have the deeper, sustained and detailed investment conversations that lead to fast funding.
Any advice you'd give to other startups raising funding?
Focus on cultivating an investor set with the expertise and insight to accelerate your business strategically and assist in building out a top tier team; not just to provide funding.
How do you think this round of funding will impact the company in the long-term?
Our current round of funding will accelerate Gamer Sensei's growth. We are already the world's first and largest mastery platform for eSports and our funding will only cement our market positioning.
Responses have been edited for length and clarity. Photos via social media and Shutterstock.
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