946. @betches Co-Founder Aleen Dreksler On Building A Massive Media Company

I recently caught up with Aleen Dreksler, the CEO and Co-founder of Betches, to discuss all things business scaling, launching into new verticals, and growing as a leader. What started off as a satirical blog for millennial women is now a massive multimedia platform and entertainment company, but Aleen and her co-founders have stayed true to their voice and community through it all. Aleen highlights her hiring strategy, how she approaches challenging conversations, and tools for shifting out of the scrappy entrepreneurial mindset and into her role as CEO. We also chat about the latest Betches venture, Faux Pas canned cocktails, and other projects Aleen is currently working on. 


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Episode Timeline & Discussion Questions

( 0:36 ) Welcome back to Earn Your Happy. Lori is joined by Aleen Dreksler on today’s episode. 

( 3:52 ) Aleen joins the conversation. 

( 4:25 ) Lori asks Aleen, “Can you just tell me a little bit about where you started and why?”

( 9:00 ) Lori asks Aleen, “How did you get help to know which direction to grow?”

( 13:11 ) Lori asks Aleen, “What would you tell people about either going it alone or getting co-founders?”

( 14:25 ) Lori asks Aleen, “Did you guys ever sit down and be like, Okay, I'm terrible at this, or I hate this, or I'm not going to do this?”

(15:32 ) Lori shouts out one of today’s sponsors, Indeed. 

( 17:05 ) Lori asks Aleen, “What is the first thing you guys made money on?”

( 17:47 ) Lori asks Aleen, “What was one of the biggest mistakes and what did you learn from it?”

( 20:12 ) Lori asks Aleen, “When is a time that you have been the bottleneck of the business?”

( 23:18 ) Lori asks Aleen, “Who was your team? And then what does the team look like now?”

( 24:51 ) Lori asks Aleen, “How have you grown as a leader?”

( 26:51 ) Lori asks Aleen, “Whether it's conversations that you have to have with your co-founders, or people who work there around challenging things, what does that look like? Do you have a system put in place around that?”

( 28:26 ) Lori and Lindsey Schwartz talk about a special offer for Six Figure School. 

( 32:27 ) Lori asks Aleen, “How do you cope with a really bad day?”

( 35:35 ) Lori asks Aleen, “What would you say is the biggest thing that has changed with you just as a person and in your business since becoming a mom?”

( 38:02 ) Lori asks Aleen, “Flash forward 15 years, what kind of impact do you want to have shown your daughter?”

( 39:13 ) Aleen asks Lori, “When people ask how do you have work life balance, what's your answer?”

( 40:49 ) Lori asks Aleen, “When did you know to start branching off into other platforms?”

( 44:08 ) Lori asks Aleen, “What's the modality in which you kind of figure that out?”

( 44:50 ) Lori asks Aleen, “Tell me about your newest venture and where it came from.”

( 48:58 ) Lori asks Aleen, “Tell me a little bit about your podcast.”

( 51:07 ) Lori asks Aleen, “Is anything that you want to leave our people with?”