This is the Leadership Journey series on the Choosing Leadership Podcast.
I believe we all have a lot to learn from each other’s stories – of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.
Embark on an inspiring journey with Jacqueline Samira, the dynamic founder and CEO of Howdy.com, as she shares her entrepreneurial saga in this insightful interview.
From navigating the aftermath of the 2008 housing crisis to spearheading a tech-driven revolution connecting Latin America with US opportunities, Jacqueline’s story is a testament to resilience and innovation.
Uncover the secrets behind her unconventional path into sales, a skill she now credits as the backbone of her entrepreneurial success.
Dive into the intricacies of building a startup, the invaluable lessons learned through Y Combinator, and the transformative power of strategic sales.
With candid reflections on the highs and lows of leadership, Jacqueline’s wisdom resonates, offering a fresh perspective for leaders seeking authentic guidance in their own journeys.
You can find Jacqueline Samira at the below links
In the interview, Jacqueline Samira shares
- “What I want to be able to do is help connect people with opportunities. That is like my lifelong dream because I struggled so hard for it myself for a year and a half after college.”
- “The first step is talking to people and communicating with potential customers and prospects. Through those early pre-sales activities, I had a really clear picture of the pain points and the solution that people would be happy with.”
- “We ended up spending close to 800,000, which is an insane amount of money in reflection on digital campaigns, on digital marketing. While it did give us customers, it’s just not the path I want to go down.”
- “There has been a problem with separating the fact that I’m still the CEO and I’m still the boss. Sometimes I have to unfortunately remind people, and that’s not a really fun conversation for me to have.”
- “I always see solutions. So if there are problems presented, the first thing I’m doing is solutioning. I think a lot of my sales acumen taught me how to think that way.”
- “I personally had 400 in my checking account. Here I am about to give birth, which babies are very expensive. Everything around that is very expensive. And it was just like this spark came in and they were shooting. Something told me, Jacqueline, go find the hidden money, go find the hidden money from yourself.”
- “Frank is the first person I call anytime I’m frustrated, or if we leave the meeting or if I leave the meeting, so that I don’t react to the teammates. I use him as my sounding board.”
- “If it doesn’t feel easy, and I think about that expression, when I think about all things, when I think about colleagues that I work with, if the relationship is not instantly working, if you don’t feel inspired and you’re both being lifted up, then it’s probably not right.”
- “Because I’m friendly and welcoming and vulnerable, there has been a problem with separating the fact that I’m still the CEO and I’m still the boss. And sometimes I have to unfortunately remind people, and that’s not a really fun conversation for me to have.”
- “I think that the most powerful thing you could do is unlock the world’s information in every single language to be able to understand every perspective.”