Fiveable closes on $615k in seed funding after a 12-month rollercoaster

Fiveable has officially closed on $615k in seed funding led by Cream City Ventures in Milwaukee.

I've seen very few times when entrepreneurs are transparent about their journeys. You see folks in the press, riding on wins, but we often omit the day-to-day struggle.

I think this is even more true for women and people of color. As an overlooked and underestimated founder, I always feel pressure to seem on top of it. When I'm in a room of mostly male, white founders, it feels almost taboo to admit that I'm struggling.

But in reality, this is not easy. Startups are not easy. 2019 was not easy.

We've been lucky with a lot of press in the last few months, and I'm so thankful for these opportunities. It was super cool to be named by Business Insider as a Top 8 Female Founder & CEO Under 30, literally months before turning thirty.

The sparkly press definitely sugarcoats reality. And because I'm a teacher first, I think it's time to open up so every one of the students we teach can see what it takes to build a startup. The key is resiliency with a lot of luck. Just keep going.

Here's my reality:

Fiveable almost didn't make it through 2019. We almost fell apart four different times in just the last 12 months. This year has been about survival mode, and survive we did.

Before I jump into the details of our journey, I'm going to spoil the ending with some good news. Because as you read on, you should know that we made it through the dark days and thrive mode starts today.

I'm excited to announce that Fiveable has officially closed on $615k in seed funding led by Cream City Ventures in Milwaukee.

But to get to this incredible win, we went through a lot. Here is the story of how our seed round almost didn't happen.

Winter 2018

At the end of 2018, Sergio & Kimmy Paluch from Beta Boom surprised me with $20k of follow on funding. I was nearing a $0 bank account, and this moment changed everything. While I could have stretched that out to support myself and our five teachers straight through the end of the school year, I decided to take my first significant risk instead.

I used those funds to launch the Fiveable House and brought in three new teammates, which was a considerable risk. Instead of a 6-month runway, we could only support ourselves through February.

But, I knew that Fiveable needed marketers and developers. I was getting by on no-code hacks thanks to Zapier, Thinkific, and Crowdcast, but we had a few thousand students and needed to level up to reach tens of thousands more.

Within the first week together, we completely redesigned our website, decided to build a web app, and published 50+ pieces of content to launch our SEO strategy.

By the end of February, none of it was enough to pay the bills. I had to let one teammate go, which was incredibly difficult, and I had to find another way to avoid homelessness. We were about two weeks away from a failed Fiveable House.

1️⃣ This was the first near-death experience of 2019.

At this point, the most important thing was to keep Fiveable alive. We had about 8k students that were watching live streams, and I knew that they were relying on us to be there during exam season. I couldn't let them down.

I made an enormous personal decision and closed out the retirement fund that I had earned while teaching. There was about $25k in there, and while it would have been useful at age 70, I had no other choice if I wanted to keep going.

I pulled the trigger and cleared out my retirement savings, which involved a $6k penalty. But we would live to tell the story. #noregrets

Spring 2019

In March, we got a call that would change everything. Fiveable was accepted to the next cohort of gener8tor in Madison, WI. I had applied on a whim when I was scrambling for opportunities, but I didn't imagine it would pan out.

We had two weeks to sell everything, break our lease in South Philly, and pack up the car to move to Madison. Fun fact: Ikea has a 365-day return policy, even if it's already built.

Gener8tor's $100k investment was more money than I had ever seen. But at that point, the most valuable part of that acceptance was the validation that we were on to something.

When you are on the brink of defeat, you have to keep convincing yourself that this is worth doing. And then you have to convince everyone else. There is nothing more validating then when someone (other than your mom) agrees that this is a business worth building. Just to be clear, though, without mom's validation, I wouldn't have even started Fiveable. Thanks, mom!

April to June was crazy busy. We met with hundreds of mentors and investors through gener8tor. In the middle of all of that, AP season brought over 100k students to our site, and we reached 25k total students in live streams. We launched a mobile app, added ten new streamers, and barely slept. I even had a feature in Edsurge. It was awesome.

Those three months were a glimpse into what could be. The whole team was fired up. By July, we moved our HQ to Milwaukee, and I officially opened our seed round. We had to raise money to build the company students needed from us.

gener8tor premiere night

Summer 2019

I kicked off July with a big win at Summerfest Tech, thanks to Marcus Lemonis. That day helped make a name for us in Wisconsin.

I spent the summer sending hundreds of emails, pitching to anyone who would hear me out, and traveling all over for meetings. By the end of August, I had pitched over 150 times and was on the cusp of closing the round.

But things didn't quite work out the way I had hoped. I had built a fragile house of cards with the few people who had shown interest in investing. But when one backed out, the whole house crumbled. In a week, we went from $400k committed to $0.

These things happen. It wasn't anyone's fault, just a series of unfortunate events. But it was a gut punch. All of my work through the summer was in shambles, we were weeks away from $0 in our bank account, and I had no idea how we would recover.

2️⃣ This was the second time Fiveable almost didn't make it.

This was the hardest professional moment of 2019. I honestly had no idea how we would survive. I had already eaten through my savings, I had no one to ask for help, and no bank would give me a loan. There were several tearful nights with the team wondering how we would make it.

I had to make another hard decision to let a teammate go after nine months together. I can't stress enough how much that sucked, but it's a tough lesson learned.

Fall 2019

In September, on the brink of certain death, we were once again saved by chance. An investor had reached out to me on LinkedIn after seeing a video of my pitch at the ASU/GSV Edtech conference from April. After a few conversations with Atin Batra from Twenty-Seven Ventures, he committed to investing $50k.

Phew. Saved again, but only briefly. That investment was enough for 2.5 months of business as usual.

With another burst of validation, I scraped myself off the floor of defeat and hit the road again, looking for investors. I sent out hundreds of more emails, pitched another 50+ times, traveled for weeks, and applied for every pitch competition and program that I could find.

The most beautiful part of this time was how much the team picked up while I was gone. Tan, Austin, and Aaron managed everything from product to marketing with the help of Sergio. All 14 of our lead teachers managed the 80+ streamers we had. And through it all, we taught almost 7k students.

By mid-October, things were looking shaky. We had about four weeks left of runway and not enough commitments to get the round closed by Thanksgiving.

As far as I could tell, I had one real shot in front of me. I was incredibly lucky to earn a top 5 spot for the Fall Experiment competition, where I pitched for $250k. It felt like the entire world rested on this pitch, so when Fiveable was announced as a co-winner, I couldn't believe it. We were going to make it.

The last two months of 2019 were intense. Thanks to the Fall Experiment, we had a lead investor, and this was a huge feat. But we weren't at the finish line yet. I had to get more investors committed.

new fiveable swag

3️⃣ For the third time in 2019, we dipped close to $0 in our bank account right before Thanksgiving.

This moment happened to coincide with my time at the 1863 Ventures Pipeline program in DC. I was hesitant about going with the stress of money on my mind, but this one week was professionally healing. The 19 other founders in the program were like a second family, and there was a sense of urgency in the room to find a way to make it. Be unapologetic, do whatever it takes, and build your dream for your users, your team, and ultimately the generational wealth I hope to create one day.

I was inspired to find a way through, so I made a tough decision. I called every one of our streamers and asked them to delay payment. It was another gut punch asking teachers to wait on extra income until after the holidays, but it's what was needed.

The most incredible thing happened, though. All 86 streamers were more than okay with that. Each of them truly believed in what we were building and understood this as a necessity. It felt like a dark time while I was in it, but looking back, I think it was a crucial moment of team building.

Of course, delayed payments weren't enough to save us from our third near-death experience. Luckily, I had one investor that genuinely believed in Fiveable. Once again, right before Thanksgiving, we were saved by Atin with another $25k bridge investment to get us to the end of the year.

Winter 2019

As we entered December, I knew this was our last chance. I had three weeks to build and close the seed round before the year ended. The momentum was there, but third chances would not be. Get it done or close up shop.

4️⃣ On December 20, I woke up with less than $4k left in our account. We were once again brushing up against the edge for the fourth time in 2019.

This time, it wasn't anyone that swooped in to save us. Instead, we saved ourselves. Six months of hard work paid off. All of the meetings, networking, deck revisions, flights, and intros were worth it.

In 2019, I pitched Fiveable 200+ times. And in the last few weeks of the year, I had five yeses. It's a .025 batting average, but it's all we needed.

As of today, we have closed on $615k of seed funding, built entirely from Wisconsin investors, and we couldn't be more excited to build Fiveable right here in Milwaukee.

One year ago, I was just starting a new journey in Philadelphia. I could never have imagined that we would be sailing into 2020 as one of Wisconsin's Top 20 Startups to Watch.

I know that my story is not unique, so many founders experience the same rollercoaster. I'm lucky to have a happy ending here; this could have been a very different post.

2020 for Fiveable is about thrive-mode. This investment will allow us to bring on new teammates, create thousands of pieces of new content, build new product features and updates, and grow Fiveable towards our goal of one million study sessions this year.

Lessons Learned in 2019

This last year has been heart-breaking, life-changing, and exhilarating all at the same time. I can boil down the year to three main lessons:

There are no rules.

I mean, there are laws and stuff, but when it comes to how to build a startup, there is no right way to do it. There are millions of think pieces and loud Twitter thoughts, but paths to success are not one-size. The farther I go, the more I realize that everyone is faking it 'til they make it. Even when they make it, they are still making it up as they go. Anything is possible and there are no rules for how to get things done. Do what feels right. That's it.

Trust yourself.

This lesson didn't come until a few weeks ago. I'm a teacher by trade, so marketing and business are not native skills for me. I went into 2019 thinking I needed experts in those fields to help me navigate. And experts can shed light on excellent tips, but no one knows your business as well as you do. No one knows your users, your vision, your struggles, or your gut-feelings like you do. Get advice, but trust yourself. You are enough.

Stay surrounded by love and support.

None of this is possible in isolation. I had at least 195 people tell me no when I pitched the company, but I always had a support system to call afterward. The only way I get to experience highs after lows are because of the love and support of my very own fan club. These people helped my team and me every day, in any way they could. Find your squad and keep them close.

Shout Outs & Thanks Yous

As I close out these 2019 reflections, I want to say thank you to each of these people for everything they have done for Fiveable and me this year. I am so honored and thrilled to have you on my team.

Yes, I'm pretending I'm accepting an Emmy. Thank you all for everything in 2019. Here's to new adventures in 2020.

The full-time Fiveable team & housemates

Tan Ho, Austin Monroe, Aaron Levin

The lead teachers

Eric Beckman, Pat DiFilippo, Kris Clancy, Megan Revello, Shirelle Tubbs, Robby May, Jamil Siddiqui, Shane Durkan, Caroline Koffke, Wes Winter, Jenni MacLean, Jenny Kostka, Candace Moore, and Kevin Steinhauser

The streamers and content creators and interns, all 172 of you!

Aaron Oculto, Aly Williams, Arianna Berman, Ashley Uminn, Landon Prokopinski, Logan Nasky, Vu Giang, Geena Kaown, Suhani Ramchandra, Jack Iorio, Sana Fatah, Delphine Lepeintre, Emily Harris , Kevin Ng, Valerie Vargas, Angie Frola, Cindy Vo, Guadalupe Aliseda-Canton, Max Kobetz, Miranda Doro, Chloe Anderson, Dacoda Burkholder, Estella Zhao, Jeriah Yu, Sam Henrichs, Christopher Ricks, Matthew Fiore, Natalie Tabb, Shivreet Dhillon, Thomasina Lester, Darren Chin, Gordon Trinh, Jeremy Kiggundu, Pooja Kalyan, Grace Binzen, Harrison Burnside, Idlania Webster, Karla Jauregui-Sandoval, Lloyd Gilfillian, In Woo Kim, Molly Sherry, Sumi Vora, Jackson Schuster, Matthew On, Katelyn Diune, Zackary Dulian, Amanda Flynn, Anusha Tekumulla, Milo Chang, Ethan Meyers, Adbel Jimenez, Kanya Shah, Nelson Alvarez, Nicholas Williams, Karthik Ramakrishnan, Anna Gonzalez, Lauren McElhatton, Dylan Black, Aly Moosa, Christina Tong, Safiya Menk, Casey Li, Tyler Fazenbaker, Angelina John, Catherine Liu, Christine Lin, Mayanak Motukuri, Rupi Adhikary, Sanders Owens, Charly Castillo, Sruthi Srinivas, Anika Allen, Brianna Bukowski, Justin Nazario, Peter Cao, Sharii Liang, Cody Williams, Kathryn Howard, Soo Hyung (Sally) Kim, Brandon Wu, Morgan Chu, Anaya Zachery, Jason Yan, Jillian Holbrook, Minna Chow, Sean Rowland, Riya Patel, Skylar Walters, Jed Quiaoit, Jacob Jeffries, Evanna Hasan, Samantha Himegarner, Bella Blanton, Danna Esther Gelfand, Akhilesh Shivaramakrishnan, Varoon Kodithala, Fatima Raja, Annika Tekumulla, Emily Pedrazzi, Rachel Ikhilov, Serene Feng, Katie Moore, Erin Brzusek, Sadiyya Holsey, Tejas Bhartiya, Jamaal Willis, Riva Shukla, Jerry Kosoff, Mary Valdez, Michael Sandler, Naderia Wade, Natalie Shevlin, Suzanne Ferrell-Locke, Abby Messerly, Bea Roberson, Edmund Scanlan, Kara Rowbotham, Larry Hatley, Meghan Dwyer, Diane Gallentine, Emilie Murray, Jeffrey Foltz, Kathleen Anderson, Kay Sheehe, Mónica Gracida, Nicole Donawho, Patrick Lasseter, Steven Kucklick, Will Pulgarin, Ariel Lane, Davida Hunt, Irye Emerson, James Zucker, Rishabh Dev, Andrew Levin, BJ Dramby, Caroline Castellanos, Deborah Maher, Emily Landers, Jennifer Durost, Kelly Dunigan, Liam Machlin, Nicole Johnston, Vicki King-Skinner, Mark Little, Donald D'Orto, Lusine Ghazaryan, Rebecca Schaeffer, June Morris, Laura Walton, Natasha Olivier, Joshua Nielsen, Kelly Cotton, Stephanie Kirk, Ashley Rossi, Bretnea Turner, John Mohl, Caleb Lagerwey, Kari Parnin, Brian Foutz, Jessica Nadzam, Christian Horner, Kate Regan, Melissa Longnecker, Peter Apps, Evan Liddle, James Glackin, Kristie Camp, Alvin, Jordyn Haynes, Dalia Savy

The moms

Julie DoAmaral & Darella Fortson

The rest of the fam

Carone Berman, Stan Berman, Harrison DoAmaral, Bob Berman, Lisa Berman, Melanie Berman, Josh Berman, Sherri Davoudgoleh, Ira Davoudgoleh, Goldie Davoudgoleh, Jacob Davoudgoleh, Robin McNamara, Sarah Monroe, and Thu Van Nguyen

The friends who answered every late-night call and text

Becky Sotello, Joel Bahr, Nicole Morales, Jaclynn Garry, Sheera Langbaum, Mitch Galli, Caroline Erickson, Liza Vilnits, Zac Brokenrope, Heather Merovich, Ivi Morales, Lailia Samimi, Chelsea Barone, and Ben Stanley!

And the mentors/professional network that made this all possible

Sergio Paluch, Kimmy Paluch, Joe Kirgues, Troy Vosseller, Maggie Brickerman, Abby Taubner, Rachel Gunder, Melissa Bradley, Phil Reeves, Art Stevens, Jason Stansell, Nic Herdrich, Dan Gawronski, Jessica Boling, Atin Batra, Craig Schedler, MC Razaire, Teresa Esser, Reed Dohmen, Dave Sachse, Matt Cordio, Nick Williams, Molly Dill, Tony Wan, Sarah Hauer, Ed Javier, Yuriy Onyskiv, Sandro Olivieri, Marie Watkins, Amanda Daering and more!

And to everyone else that followed us, liked our posts, attended our streams, shared our site, bought us lunch, caffeinated us, stayed subscribed to our emails, and more, thank you.