ActiveCampaign CEO and founder Jason VandeBoom joins Scott back on the pod to talk about the latest news - announcing a whopper $240 million Series C round led by Tiger Global to scale up its operations and continued growth with customers (up to 145,000 active customers). As an 18-year old business, ActiveCampaign is hardly an overnight success story, but has gradually built up a strong user base that has skyrocketed in recent years fueling the strategic investment rounds after years of bootstrapping. On this episode you'll hear Jason talk about AC's journey, helping business make decisions closer to who they are and serving the customer a better experience and building towards the future of marketing.

For many of us, it's been a long long time since we experienced the office setting. The pandemic has pushed large swaths of the labor force into work from home settings, some permanent and some companies promising flexible policies. So just what is the return to the office going to look like? We dive into that question with our longtime friends Brad Serot and Tony Coglianese from CBRE. The answers may surprise you, studies suggest a partial return to the office - a couple days a week - is a popular preference that gives workers a mix of in-person community building with the flexible, remote lives the other days. Brad and Tony share the insights they've learned about how tech companies are officing, investing in startups through LongJump, how they've managed their personal lives through the pandemic among other things on this fun catch up episode.

Andrew Degenholtz joins the show to talk about his company eMags. eMags Newstand provides a seamless digital experience for magazine readers to consume their favorite subscriptions enjoyably from their phones. Scott catches up with Andrew to talk about the state of journalism, fixing broken media business models, how eMags can inject new life into the writer/creator economy and how they've built a legit subscriber base.

Scott talks to Alda Leu Dennis, general partner at Initialized Capital. Started by Reddit co-founder Alexis Ohanion and Garry Tan, Initialized was borne out of their early Y Combinator days and has become the "honeybadger" of venture with an emphasis on changemaking ideas with over 200 companies in their portfolio. Alda shares her journey from Texas to Stanford, getting the venture bug after meeting Peter Thiel and becoming a GP at Initialized. Alda and Scott also dive into coastal vs midwest VC comparisons, the impact of COVID-19 and making funding more remote-and accessible- as ever, building your brand in public vs privately and what she looks for in a founder and company idea that can impact the world at scale.

Lisa Carmen Wang has learned a lot as an accomplished gymnast, founder and investor. And after getting her first company SheWorx acquired by our friends at equity crowdfunding platform Republic, she's on a mission to democratize investing and financial freedom to those typically kept outside of start up investing. Besides her current role as Head of Brand and Communications at Republic, she's the host of The Confident Investor podcast where she seeks to educate the next generation of female & diverse business leaders. Lisa joins Scott on the show to talk about financial confidence, empowerment and how to give people the tools to gain their financial freedom.

When gyms big and small closed down over the past year, most people are confined to continuing their exercise routines with body weight workouts and name-your-stationary-bike routines. But finding a place to exercise with all the standard gear and weights you could rely on at your local gym are basically impossible to find or sold out. This sparked and an idea for Jake Goldstein, a Chicago-local entrepreneur saw an opportunity to get people back in the gym with modern equipment, privacy, cleanliness and even personal training - all within a shipping container. His company BOLD builds out shipping containers with all the gear, amenities like Wi-Fi and screens that you can hook up to have a personal trainer engage with you during your workout remotely. Based in Chicago for now, these containers are portable and can be placed in new locations as needed. Jake comes on the show to talk about how BOLD is working, making money without costly big box gym membership fees and condensing the gym experience to modern demands.

When David McFarland got a job as an actuary out of college, he was working at an insurance firm where he first saw how data wasn't being optimized. Later after working alongside Kyle Nakatsuji at auto insurtech company ClearCover, he saw how Kyle's model could apply to all of small businesses and more importantly, saw how small businesses were overlooked. David joins the show to talk to Scott about why big firms overlook small business owners and self-proprietors, how Coterie tailors to them, being a recovering actuary and tips on getting a firm response the right way.

It's said these days that the pandemic moved the world forward five years in five minutes, and companies like CASHDROP are the ones leading the charge by rapidly adapting to people's needs. CASHDROP helps you create custom, shareable store links that link to your store and can create "drops" by revealing new products, foods, courses etc without paying commission fees. Ruben wants to democratize small business and makes money by passing on a small convenience fee to the customer. Ruben and Scott get into critical conversations on the shortcomings of e-commerce, the problem with Midwest VCs, how to actually support minority founders, Ruben's dreams to rename Sears/Willis Tower "Immigrant Tower" and more.

Quevos co-founder Nick Hamburger has taken his company he started out of his college class and kitchen to the stage of Shark Tank in a few short years. And won! Nick comes back on the show to talk about what's changed with Quevos, leadership lessons that no one prepares you for, how he got a guest Shark to say yes and the challenges of running your own company.

Label Insight co-founder Dagan Xavier joins the show to talk with Scott about the how his company is providing better, clearer information to consumers to find products that match what they need (or eliminate what they can't have) while also empowering brands with better data on their customers. Dagan shares how he initially came up with the idea helping his dad sort through different foods and pastas to figure out what he could eat with dietary restrictions from his doctor. Made a spreadsheet and realized there was some real insights that other people should have and be able to use for similar needs and general transparency.