Not many can say they rode the Rise of the Rest tour bus with Steve Case and the Rise of the Rest delegation. In fact, of about 30 passengers throughout the ride, I was chosen to ride along. Since this was the Rise of the Rest’s 8th tour and they select 8 finalists for the pitch competition, it is fitting I share with you the top 8 Moments of being on the Rise of the Rest Bus.
8. The St Pete startup scene is unified, passionate and goes above and beyond in telling the story of the city.
Rise of the Rest (ROTR) kicked off at Station House in St. Pete where the city’s Major Kriseman named Presence’s CEO Reuben Pressman as the St. Pete’s first Entrepreneur in Residence. Not to be forgotten that the Mayor hosted Wave’s 2018 TechDiversity cohort and one of the ROTR partners mentioned they had previously met J.P. Dubuque, the President of the St. Pete EDC when he brought St Pete startups to a Nashville tech conference. It was hard to miss Inside Out’s Chad Nuss wearing a “St. Pete vs Everybody” shirt under his blazer when hosting the delegation. The day culminated at two St. Pete based companies, Presence and RankMiner and both companies advocated for the city during their pitch. It’s clear that St. Pete is on fire and couldn’t be better partners with Tampa in making our Bay Area shine.
7. Steve Case is prepared, focused, personable, and tireless.
Tampa Bay met Steve on Day 3 of the Florida/Puerto Rico tour where the delegation rides the bus from 7am-7pm. During each stop, he speaks and intimately engages with the CEO/Founder of each company. He asks spot-on questions, creates moments to bring levity to the environment, like lounging at Penny Hoarder’s office or playing air hockey. Although he takes the Rise of the Rest mission very seriously, he doesn’t take himself too seriously. The entire tech ecosystem in the country is fortunate to have him. He gives his time, talents, and treasures back to tech entrepreneurs. I believe Steve’s greatest legacy will no longer be his founding of AOL, it will be the movement he created with the Rise of the Rest.
6. J.D. Vance, best selling author, is the perfect compliment to Steve Case and is very approachable and humble.
We often talked about our kids and sports. J.D is the Managing Partner of the Rise of the Rest Seed Fund and author of the #1 New York Times Bestselling book Hillbilly Elegy. My biggest take away from my time with him was the numerous insightful questions he asked while at our table. He spent a lot of time diving in to try to better understand the Tampa Bay tech ecosystem and landscape.
5. The Debate on Bootstrapping vs Funding continues.
The first two visits on the tour were to the Penny Hoarder and Inside Out, two companies who have bootstrapped their way to success without any outside capital. On the Ferry, I sat with J.D Vance and Eric Rabivonitz, who just exited Lilypad, and Eric told the story of bootstrapping Lilypad. I think it highlighted, in a very organic way, the story that we don’t have enough startup or seed capital options yet in our region, however, many companies have grown in spite of the funding realities.
4. Two ways to skin a $50M raise… Peerfit “vs” A-LIGN.
The funniest part of the day had to be when introducing Peerfit’s Ed Buckley and A-LIGN’s Scott Price to to J.D. Vance as I wanted him to hear two stories of local companies raising capital. Both Peerfit and A-LIGN have raised over $50M in capital. Ed tells this incredible and detailed story of first getting contributions from friends and family, the challenges associated, the many rounds he had to lead – the list continues. The idea has been sparked to have them do a Round Table where they both share their different journeys.
3. Taking the Day In.
It’s so easy to let the day go by while balancing posting on social and ensuring you make as many introductions from Wave companies to the Rise of the Rest as possible. My top two personal “living in the moment” memories were getting a picture with Brian Kornfeld and Lakshmi Shenoy before getting on the bus. We were all giddy and so genuinely excited. We went on the opposite side of the bus to point to the Tampa Bay part of the Bus signage while almost getting hit by a car – that’s dedication at the very least. I got to spend a few minutes with Tony DiBenedetto on the ferry ride from Tampa to St. Pete and I always enjoy our candid talks and although he could have been talking with lots of other people, he wanted to share with me an idea for his Think Big for Kids charity. Tony has been a pioneer in our ecosystem as a founding chair for the Wave and TBT, in addition to building and scaling Tribridge, so it was great to see leaders like him, Linda Olson, Tom Wallace, Marc Blumenthal and others get to enjoy their time on the Ferry with Steve Case.
2. The ConnectWise Pitch Competition Story is quite fitting of our ecosystem’s growth.
The original pitch competition venue had a capacity of 300 people and sold out in two days. I was able to connect Rise of the Rest with Connectwise and we had an intro call a few Mondays ago. Between Monday and Thursday, 40+ email exchanges had taken place and approvals from marketing teams, legal, and landlords had been received. To see two amazing brands come together in just 4 days to make the Main Event double the capacity to 600+ attendees amplifies the belief in our ecosystem and the willingness to roll up the sleeves. The extra work both parties put in came to fruition for an incredible night of entrepreneurship. The fireside chat with Jeff Vinik and Steve Case met all expectations as they did a deep dive into Tampa Bay. The Pitch Competition exceeded expectations as all 8 companies did an incredible job and there were no weak links. All rose to the occasion and you can tell they each became friends during the process. I was truly humbled when Immertec’s CEO Erik asked Richard Munassi, Linda Olson, and I to join the Immertec team on stage for a picture with him and the $100k check.
1. This entire experience was WAY more than “just” a day.
Several people have shared “but Rise of the Rest only comes to town for one day.” Although technically true, they spent 6 months carefully planning the trip in advance. They are very engaged and ensuring all key stakeholders are included. They then review 135 startup applications for the pitch competition. They fly in an advance team who gets all A/V, signage, etc. done in advance of each stop. They have things planned to the minute. Steve Case himself spends 5 days in a row on a bus from 7 am to 7 pm, no way he needs to do that, but he wants to! This was way more than a day, but the start of a deeper relationship. In many other cities, Rise of the Rest end up investing in more than one company.
I dedicate this post to one of the most tireless and relentless people I’ve ever met, Mark Rucci, the Community Manager for Rise of the Rest. He is so professional, friendly and dedicated. Each time I got a late night or early email or text from him, I knew he was doing that “Times 5” as he had 5 tours to plan. He treats you like your the only person in the room although he has 100 things going on in his mind. I had the chance to first meet Mark as I got to host him for a day at Synapse and I now call him a friend who believes in what we are doing. Special thanks as well to Anna Mason, partner with the Seed Fund. She recently had a baby and that still didn’t stop her from being so hands on.
