My name is Colby Berthume and I am the co-founder of Plain Sight, an event technology platform for event creators to sell tickets and sponsorship rights for their events. 

I have had roles in strategic planning, communication, and growth marketing at companies from early-stage startups to large, fast-growing companies.

We have raised a $1M pre-seed at a $6M valuation cap — all from angels. We raised funding in the thick of COVID. 

We got our first check while in the ideation stage in 2019 — we didn’t launch until 4 months before the pandemic hit.

We took on $500k for an in-person activity, and then took on another $500k for our pivots. We’ve raised $1M, but it definitely doesn’t feel like we’ve achieved that.

We started working on this idea in the Spring of 2019.

My co-founder and Plain Sight CEO James Chapman had been discussing the idea with Dan Gilbert (owner of the Cleveland Cavaliers) — for whom we both worked.

Dan gave us an initial $500k to get the initial product ready to go to market — with the intention of investing more as we gained traction. 

The first check hit our account in early 2020, but once the pandemic took off we had to pivot.

Our initial strategy was to build a platform that allowed event creators to sell tickets for their events.

We had target cities that we were going to begin with and gave ourselves revenue targets to hit over the course of 18 months.

We focused on investors who specialized in media and event businesses, with a sub-focus on networking and connectivity. 

Since we were still very early, we focused on angel investors — especially angel investors that we had a level of familiarity and trust with.

Rather than just targeting the big name investors, we thought it was important to work with people who we had alignment with.

Our situation is a bit unique because our first investor was Dan, so we started out with a network of potential investors that we already had some relationship with.

We didn’t have to ask for many introductions — Dan was our champion who introduced us to the majority of people we raised from.

Those people then shared what we were building to their network because they just believed in it so much.

We have reached out to over 100 investors in the history of the company. About 30% of those led to meetings — 20% of those meeting resulted in a check. 

We pitched the team above all. Myself and my cofounder — James Chapman — have a lot of experience in this market and know it better than most people.

We also had a differentiated perspective on what the business could be compared to the existing incumbents — we were able to counter-position ourselves that way.

We’d offer to work on a small project to show them how we operate and then overdeliver on the execution. That went a long way on them buying into our ability to make this work.

We tried crowdfunding and other marketing tactics, but they did not really move the needle.

The thing that worked best for us over time was perseverance and surviving as an event-based startup through a pandemic that essentially shut that sector down. 

We kept finding ways to survive and stay on potential investors’ radar.

Seeing us find a way to keep the company going really helped investors believe in the team and the idea.

The fact that we are both non-technical founders didn’t help things at all.

Investors tend to prefer that at least one of the founders has a technical background — the fact that neither of us did was a sticking point that came up a lot.

One way we overcame this was by trading a bit of equity in the business for a partnership with Shrine Development Company.

The founder of Shrine is a really experienced founder who has a stake in the business. 

When we were hiring technical leads, he did the onboarding and the training. Having someone like that involved at that level has really helped.

The fact that we’re based in the Midwest was challenging as well because proximity isn’t something that’s worked in our favor.

Getting fundraising meetings was easier during the pandemic than it was beforehand.

You had to fly into various cities to meet with investors. During the pandemic VCs would be on Zoom all day and stack their calendar with meetings.

That made it a lot easier for us to get more meetings without having to disrupt what we were working on day to day.

In order to succeed when fundraising you have to effectively communicate what makes your company — and perhaps more importantly — what makes you unique.

People can put together a great pitch deck with their roadmap and financial projections, but the truth is that most of the time there are pivots — things do not go the way you planned.

Investors want to know what is going to make you capable of handling those moments.

Rather than trying to paint the most impressive picture of yourself and your accomplishments, show some scars. 

People can see through the facade and will wonder what they are missing — if you are more transparent about those types of things it will set them at ease.

Jason White — former CMO of Fanatics and Beats by Dre — is the best partner for any startups that involve brand partnerships. He is a frequent check writer and a very good partner. 

The most important point for me is to read up on as much industry news as possible to know what is getting funded, who is writing checks, and what the funding amounts are. 

This helps always knowing in real-time what is happening to allow you to better gauge your own company. 

One resource I follow is Silicon News — which provides a weekly briefing on Silicon Valley funding, merger, and acquisition news.