How about we base the discussion around. recent fundraising. how it feels to be validated. the adversity you’ve had to face. some personal details (like your choice to be sober). Things to note prior to our recording. Bright setting, and real, well organized setting/background is crucial. Earplugs are highly recommended & will prevent echo. In order to avoid lag/disruption, closing all tabs/programs is ideal. We’ll be using Riverside, no download required. We can keep it real, fast paced, and to the point = 📈. Ideally we’d want to keep this within 15 mins. Intro. “I’m joined by my man, Joe Steilberg, Co-Founder of Twos. His company recently closed a $1.4 million pre-seed round led by TampaBay.Ventures. In light of the news, I thought I’d ask Joe a couple of questions on the struggles leading to this monumental point of validation. Questions. Joe, founders are always doubting themselves. No one builds a start-up maintaining absolute conviction, a 100% of the time. There’s always those moments when vulnerabilities start to overwhelm you and you begin to question the viability of your idea or business. How did you fight the mental battle leading up to now? That's a great question. Needing to stay grounded and confident is something every founder struggles with. For me, my co-founder Parker has been instrumental in helping me stay focused on what we are building. He is my anchor and I am forever grateful for his partnership on this exciting journey. The tech industry has almost universally embraced a remote-first world—especially true for startups. What value did you guys find in tying yourself so closely to Tampa Bay & its ecosystem? We actually landed in Tampa by chance when I took a job with a private equity firm here and Parker was working remotely for Google. What we found is a blossoming community of like-minded entrepreneurs we have been able to connect with through groups like the Embarc Collective, Tampa Bay Wave, and the University of Tampa Spartan Incubator program, which is where I am right now. We have loved the support from the Tampa Bay community so we want to return the favor for years to come. You’re a first-time founder. What was it like raising funds? How did you even know where to begin? And What are some key learnings you’d share with others trying to raise? A lot of reading, trial and error, and passion for what we are building. We have tried everything from going to events, warm intros, and even cold outreach. But what proved to be the most successful was starting early and consistent updates. We had our first conversation with Tampa Bay Ventures about a year and a half and 4900 users ago - luckily, we had the insight to start a monthly “Twosletter“ where we would update people we were talking to with our progress. When our growth started to kick in, we reached back out and they decided to lead our first round. All of our partners have been amazing thus far and every “no“ we got is just another addition to the Twosletter for a future conversation. What does one do with $1.4 mil? I know branding and marketing is a big focus. How do you plan to allocate spend and ensure it doesn’t all evaporate on paid user acquisition? Right, cause there's an endless graveyard of companies that have gone defunct doing exactly that. Absolutely. We are thrilled to say that all of our growth has been organic via social media and word of mouth. So we know people love the product. We are still moving very slowly toward paid user acquisition - and anything we think we can accomplish ourselves, we will try first. Which is why we really appreciate you having Parker and me on to share Twos with more people. But paid marketing is inevitable because our organic audience is relatively small and eyeballs cost money. Besides that, we will be starting conversations with designers, social media managers, and anyone else we feel can be a complementary asset to the early growth of the company. Why not bootstrap? What's your cost-benefit analysis for raising funds in exchange of up giving up discretion, having to answer to investors, and not having as much skin in the game? What I’m wonderings is, at what point does being a founder feel just like another job? That's a great question. I feel like when you are working on something you love, with a great co-founder, that can help millions if not billions of people, it never really feels like a job. There are plenty of things that are less enjoyable than others but it's all part of the bigger mission. As far as giving up equity, I do feel like that is a very funny misconception by most people. It's almost like as a society we celebrate fundraising rounds although in reality, it is selling a little piece of your baby. For us, it was a matter of scalability and time. We knew we would need capital in order to reach the masses, so we ran scenarios for the next 3-5 years and felt confident in the decision we were making.