Lessons From Two Fundraising Rounds and $7.3m in Capital Raised

As part of our Founders + Funders SF 2019 summit, held in partnership with Seneca VC, we brought together an exciting group of startup founders and investors for a day of learning, networking and growth.

We were joined by Kristina Jones, CEO and Co-Founder of Court Buddy, a startup that quickly connects people to solo attorneys at rates they can actually afford. Originally based in Miami (now in San Francisco), Court Buddy raised a Seed Round in October of 2017, and then quickly turned around and raised a $6m Series A Round in one year’s time. We’d previously talked with Kristina when she was at 500 Startups, and were excited to get the real update. We chatted with her about her experiences in fundraising and running a startup in general. Kristina was joined by Karina Cabrera Bell, Co-Founder of OpenAccess, who facilitated the conversation.

Karina: It’s Friday. Is everyone excited? My name is Karina Cabrera Bell, and I’m the founder of OpenAccess. We’re working with companies to create gender equity in the workplace. We’re no longer allowing people to say they can’t find women and women leaders [laughter] because that’s just not true. So we’re hiring women and creating spaces in the workplace so that women can do well and thrive, and not simply have that one token woman. We want them to do well.

I have to tell you about Kristina. When I first moved to San Francisco about two years ago, I really saw a need to highlight women of color and moms of color that are just badass. Can I say that, badass?

Kristina: Yes.

Karina: And I did all this research, and she was the first one I found. I asked her if I could highlight her and let everybody know about her and honor her, and she immediately said yes. And then it turned out we lived in the same building [laughter]. So it was meant to be.

Kristina: Now our kids play together.

Karina: So we became friends. Let’s get into it. Tell us about Court Buddy. What is it? How did you start this?

Kristina: A little overview. We all know the legal industry is a hot mess [laughter].

What people don’t know is how many people actually go to court alone. Every year, there are 129m Americans who go to court and stand in front of a judge without representation. So we launched Court Buddy in Miami, Florida after my co-founder – a solo attorney – started recognizing a lot of people were approaching him right before going in front of a judge to read over their paperwork. I’m talking seconds before going in front of a judge. And after seeing that these people were about to either go to jail, have their children taken from them, or be removed from their homes, we realized it was a major issue.

So we started asking the question, “Why don’t you have an attorney?” and the responses we were getting back were, “I don’t know where to find one.” or “I can’t afford an attorney.” And even if they could afford an attorney, it was so blurry to them, we were hearing things like, “I don’t want to put my life savings into something and I don’t know the outcome of.” We quickly realized that there was a disconnect between people needing and actually understanding the legal industry.

We started doing our research and realized this wasn’t just a Miami problem, and asked ourselves how could we solve it. We built the resulting platform where we connect people with a local solo attorney for an unbundled service. An unbundled service is a single court appearance, single document draft, a single deposition. So essentially, attorneys no longer have to appear from the beginning of the case to the end of the case, which was making it really expensive. They can now appear for a single need, which makes it more affordable.

What’s even more amazing is that we don’t allow attorneys to charge a retainer or an hourly fee. The client can come on to our platform and get instantly matched for a flat rate based on their budget. So now we’re talking $200 for a single court appearance, and they can even pay that over time. We’ve essentially built a platform that instantly connects people to a solo attorney at a rate that they can afford.

What we’re doing is making the legal industry transparent, affordable, and now predictable.

Kristina: That’s awesome. And so how did you know that you were ready to start fundraising? At what point did you decide to do that?

Katrina: In 2015 – maybe a couple days after we launched Court Buddy – we started receiving revenue. We had met this investor group in Miami and they were so excited, so they were like, “Come pitch us.” We knew nothing about fundraising, but we said, “Okay. Let’s go through this experience.”

Karina: Wait, so they found you?

Kristina: They found us, and it was a complete disaster [laughter]. Like literally, I still get shivers when I think about it. We went through the due diligence stage. We prepared for a whole week. We were nervous. And that first due diligence meeting, we could tell they didn’t even open the first page. They didn’t even look at the work that we had done to prepare. And then the first question out of an attorney’s mouth was, “Why would anyone pay for this?”

Karina: Oh my gosh.

Kristina: And every single question, everything that we said, it was combative, and so we thought , “I this what it’s like? We don’t want to experience this.” We basically vowed to never fundraise again. We thought, “We’ll bootstrap this thing until the wheels fall off.”

But then it got to a point where we needed the help. The site was getting a lot of traction. We were generating revenue, but we needed the help in terms of staff to support our members.

At that time, 500 Startups came on our radar, and we applied. We actually got denied the first time. We didn’t understand what it was like to pitch to a Silicon Valley investor. From their feedback, they told us, “Look, you need to make it concise, sharp. Tell us your your KPIs and everything upfront. And don’t just ramble on.” So we learned from the first failure.

We also got an intro from another founder who’d gone through 500, and came out to Silicon Valley in 10 days. Like, literally moved here in 10 days with a 16-month old. That’s another story for another time [laughter]. But that’s when we realized, “Okay, this is the time. We have the support. Let’s try this again.”

Karina: That’s amazing. So the kid thing is a different story [laughter]. Talk to us about the strategy and the process. You decided you were going to pitch. What did you do to prepare?

Kristina: For the seed round, 500 Startups definitely helped prepare us. I don’t know if you know about that program, but if you’re from outside of the area, you move to San Francisco, it’s a four month program. Every single day they’re giving you content, they’re introducing you to investors, they’re preparing you for your seed round.

Early on, Monique Woodard of 500 Startups approached us and said, “Hey, guys. You look a little different from everyone in Silicon Valley, so I’m going to give you a little bit of advice. Don’t just go after the funds that say that they’re looking for minority founders,” because at that time, there were only five. She said, “This is a numbers game. You need to reach out to everysone. Cast a wide net and see which fish lands in your net.”

So we reached out to probably a total of 200 investors. 13 ended up coming into the round. Our Seed Round was $1.2m, and it included angel investors, family offices, and VC firms. Lightspeed and Gingerbread Capital came into our seed. It was a variety of different stages and different funds, different check sizes. We learned a lot throughout that process on what it took to get a $25,000 dollar check, what it took to get a $250,000 check. We definitely learned a lot.

Karina: So I assume you got a lot of nos, or…

Kristina: Oh yeah.

Karina: Because sometimes I hear that VCs don’t say no, they just don’t respond [laughter], and I’m curious.

Kristina: Digging back into our process, what was helpful was to build a spreadsheet. In the early days, we just went on a hunt for firms that were interested in marketplaces, or if the firm was interested in legal tech, or if they were interested in consumer startups or women-led startups. We started digging one by one through that list, and we would go on LinkedIn to try to see if we knew anyone that was connected to anyone in that firm. We went through 500 Startups, who had connections, and then just put out the word to try to get a meeting.

There were a lot of– there was silence. There was, “You’re too early.” But what we learned in the process was, even though we received a no, we could quickly turn that into a yes by asking them to refer us to someone who they thought would be a yes. So out of every meeting, we got a list of other VCs that we could talk to. So we never left a no meeting without something to follow up with, which was great.

Karina: And did you have a team helping you through this, or was it you and James?

Kristina: For the seed round, it was just James and I. And we quickly saw the value of having a co-founder. To have a successful raise and a quick raise, it’s great if one founder can do it full time while the other founder is continuing to work on the business. If you’re a solo founder, it can be done, it’s just going to take a lot more time. But also, something in the business might give if you don’t have a team around you. So it’s great if you can find the support.

If you are solo founder, get interns. Get someone who can really help support your business while you are 100% fundraising.

And then for our A, of course, with the seed round, we were able to hire. At that time, I think we had an additional six team members. So if the both of us had to go out to close the round, we didn’t have to worry about the business taking any dips.

Karina: And what was your approach? Did you find that your approach was different when you were pre-seed and then A? What was the different approach there?

Kristina: With the seed, it was– we were brand new to Silicon Valley. It was a lot of introductions, telling people about the problem, telling people about our solution. A lot of just first-time interactions.

Then what we did from the seed to the A – and this was strategic – is we put out a monthly newsletter to anyone on that list that we had built. So our current investors, potential investors, even investors that said no. And in that newsletter, we had our monthly KPIs, we had some asks. If we needed help with anything, we put out the ask. Newsworthy things, like this event. In fact, our newsletter went out today, and this event was included in it. Any press that we got. But the most important aspect was, at the bottom, we had a thank-you section. So any investor we talked to throughout that month, we thanked them.

What was happening was it was causing other readers of this newsletters to want to come and help so they could be a part of this thank-you section. By the time we announced that were ready for our A, everyone knew what we had done for that 12 months. So it was a much easier conversation. And the replies just started coming in, “We’re ready. Let’s talk. Come to us first.” So if we hadn’t done that process, I think we would have been starting from the beginning of introducing ourselves and having to talk about the last 12 months.

Karina: That’s awesome. How about any bias as a woman of color here in Silicon Valley asking for money? I’m curious, what was your experience, and how did you handle it, if you incurred that?

Kristina: There were two things that would happen throughout the seed process.

One was when people would ask if I was my co-founder’s secretary [laughter]. Yeah. I mean, I have an amazing co-founder. He realized this, and so when we went into a meeting, he would introduce me first. So that was just not even a question.

And then there were some times, if it was an all-male investment team, that they would ask a question and I would respond, and they wouldn’t even look at me. They just look at James.

Karina: Oh my god.

Kristina: And so there was a moment during our raise where I was like, “If there isn’t a woman in the room, I don’t want to go. James, you’ve got it.” He would say, “Oh, we’re meeting with this firm,” I would look them up really quickly and try to see if there was a woman as a partner.

Karina: Oh wow.

Kristina: And if there wasn’t, I was like, “You got this [laughter]. You got this one.”

Karina: And this is just recently, right, like a few years back?

Kristina: Yeah. Yeah. A couple of months ago [laughter].

Karina: It was that recent? Oh my God. So tell us any lessons learned from this experience. If you could go back, what is that one thing that you would tell yourself?

Kristina: I’d use a couple things [laughter]. In the seed process, finding your lead is so important. It helps speed up the process and it helps you to not have conversations with firms that aren’t really even going to move the needle for you. So we learned quickly to ask, “Do you lead?” and to go on a hunt for the lead first, because once you have your lead, that’s like you’re partner; they’re going out with you, they’re opening up their rolodex for you because they want to help you close this round. I

If you’re speaking to a firm that ends the conversation with, “Oh, sorry, we don’t lead. Go find your lead first and then come back,” what we learned — or what we should have done in the early days- is ask, “Okay, well, who have you co-invested with that leads?” Either you can get a list of people that they’ve invested with that lead or ask for the introduction, and I think that’s a good indicator or if they’re really interested, if they say, “Yes, we’ll make the intro.” If they say, “I don’t know,” then you may want to move on [laughter].

Karina: That’s awesome. Any final tips for the folks in the room? And by the way, I’m curious to know, are there any founders, any entrepreneurs? Awesome. Awesome. Awesome. So any final tips as these amazing entrepreneurs prepare to fundraise?

Kristina: Yeah. Know that it’s a process. You really have to run the process like your business. I don’t think you can dabble in it and then step out. You have to dedicate, really, I would say, three to six months to go full-on with this, and do your preparation ahead of time, build your list.

One thing I didn’t say is, when we were going for our A, our seed investors actually built the list with us. They were in this document adding firms, adding notes, but really being strategic about it. And with this list that you’ve built, put in your notes because one of the things is the follow up. I think that is the part that got kind of blurry, is following up with the firms that you meet with. If you have your notes, you can put on your calendar, “I’m going to meet– or I’m going to you know respond back or check back in a week.” Really being diligent with your list and your process.

Also, asking other entrepreneurs for intros, I think that’s the strongest intro you can get, is when a firm’s investment gives the intro. For example, if you meet a first round company and you want to be introduced to first round, rather than having another firm that’s not investing in you make the intro, have that entrepreneur make the intro for you.



The Switch Editorial Team.

Straight to your inbox.

The best content on the future faces of tech and startups.

"*" indicates required fields

This field is for validation purposes and should be left unchanged.



Join the Angel Sessions

Develop strategic relationships, build skills, and increase your deal flow through our global angel group and investing course.