From Start-Up to Grown-Up

Jake Stein is the cofounder and CEO of Common Paper. Previously, he was the co-founder of RJMetrics (acquired by Magento, then Adobe) and Stitch (acquired by Talend). Before RJMetrics, Jake worked in venture capital, started a landscaping business in high school, and was the 44th ranked table tennis player under 21 in New Jersey; achievements of which he is equally proud.In this episode, Jake discusses the pros and cons of distributed teams, the questions that he and his co-founder asked before they started their company, and the challenges he ran into once his former company was acquired. You'll also hear Jake's biggest mistake, how he invites company feedback parties, and all about Whale Wednesdays.[01:27] Entrepreneurship Origins[03:32] Aligning Company Plans[11:33] The Emotional Battle of Running a Business[28:03] Written Feedback vs. Verbal Feedback[33:23] Fostering Company Culture[45:36] Jake’s Biggest Professional Blunder[58:05] The Importance of Self-Care[58:51] Advice for New Business OwnersTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scriptsConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Zvi Band is the co-founder and CEO of Contactually, which has been acquired by Compass. He is also the author of Success is In Your Sphere. His new venture is called Talk Social, which is focused on bringing humanity back together.In this episode, Zvi and I had a conversation about how he got onto the path of entrepreneurship, how he learned to see himself as the leader, and the limits of transparency. Zvi and I also get into a real talk discussion about co-founder dynamics, mental health, and his surprising advice to founders who are getting ready to sell their business.To hear more from Alisa, sign up for her newsletter!Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Matt Blumberg is the founder and CEO of Bolster, a new talent marketplace for on-demand executives launched in 2020. Before Bolster, he was the CEO of Return Path. He has authored two books, namely: The Startup CEO and The Startup CXO.In this episode, Matt will take us through his entrepreneurship journey. He will give us in-depth details on how they founded Return Path, how they built the company culture, as well as their exit from the company. Matt also shares how he creates a support system, learned to say ”no,” and became a two-time CEO.If you were to sell your company today, would you feel like you are giving away your child? Today, I’m joined by a man who founded a company, built it up, attempted selling it and failed, went back to rebuilding it, and sold it years later. Meet Matt Blumberg!Matt is a founder and CEO of Bolster, a new talent marketplace for on-demand executives launched in 2020. Before Bolster, he was the CEO of Return Path. Also, he has authored two books, namely: The Startup CEO and The Startup CXO.In this episode, Matt will take us through his entrepreneurship journey. He will give us in-depth details on how they founded Return-path, how they built the company culture, and their exit from the company. Also, he will tell us how he creates a support system, his journey to learning to say, "no” and how he became a second-time CEO.Key Talking Points of the Episode:[01:36] Getting to know Matt[03:27] Matt’s growth path in leadership[09:30] How Matt learned to say NO[12:39] How to build a support system[13:23] What’s the difference between a coach and a mentor?[15:10] How Matt handles difficult conversations with his employees[21:20] Coaching someone is about to get fired[29:30] How Matt built the company culture at Return Path and how it evolved[40:16] How Matt deals with difficult setbacks and bad moments in his day-to-day life[41:57] Transparency and authenticity[43:27] Matt’s favorite failure[51:05] How Matt sold Return Path[56:25] What is it like to be a second-time CEO for Matt?[01:02:58] The most challenging role for Matt in his current role[01:04:42] Matt’s book, Startup CXO and why it is important [01:10:43] What Matt wishes he knew earlier on his journey[01:11:15] Matt’s message to other founders, as they embark on their journey to grow into leadersQuotes from the Episode:“You’re never done growing as a leader all of us are works in progress.”“The most important conversation to have with an employee or an executive who is not doing well is the conversation you have before the one you fire them.”“The best way to deal with a bad moment is to wait a few minutes. Something else is going to come along and replace it.”“When you make the hard conversation early, that means the later conversation is easier.”“Don’t be shy about asking for help. There are a lot of people around you who know a lot more than you do about a lot of things that you’re doing.” Grab Matt’s Books: Startup CEO: Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Learn about Alisa's new podcast, From Start-Up to Grown-Up, where she interviews founders about the journey from their beginnings as a fledgling business to thriving companies that are leading the way.Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon