Elizabeth McCalley on professional resilience, intuition and gut feelings, handling no-win situations, and culinary experiments (#49)

Elizabeth McCalley_website

In this episode of Her HypeSquad with Bosstrack, we have the pleasure of bringing you insights from Elizabeth McCalley, the CEO of StartStak.

This conversation covers quite a bit, from the art of professional resilience to the often underestimated power of intuition. We also talk about the profound significance of time and handling no-win situations. But it’s not all business. We also venture into raising chickens and culinary experimentation.

Contact Elizabeth

LinkedIn: @emccalley

Website: www.startstak.ai

About Elizabeth

As the CEO and Founder of StartStak, Elizabeth is a results-driven executive enabling strategy and go to market for early stage companies.

She is AI-native and excels in developing new markets through use of emerging technologies. She brings extensive experience in nascent markets, industry solution development, marketing, partnerships, and alliances.

Elizabeth has a passion for developing new markets and is on a mission to broadly enable entrepreneurship through a new business design. StartStak is Founded for the Founders.


Backyard chicken culture
Glass ball theory
Radical Candor by Kim Scott
Rogan Josh
Business Wars podcast
Bad Blood
Even the Rich podcast
Last Week in AI podcast
ChatGPT Plus
Pillars of the Earth by Ken Follett


[02:41] Elizabeth introduces herself
[05:46] Resilience, growth, and moving through our seasons of change
[08:35] A time in Elizabeth’s career where she experienced change
[13:59] Managing the glass balls vs. rubber balls in your life
[15:44] Balancing career and family as a working mom
[17:47] Pressure of social media and finding your own path
[19:25] Communicating your needs to your boss
[23:21] Finding the win-win when going into a conversation
[24:09] How to lead in no-win situations
[27:00] Navigating risk and rethinking failure
[30:54] Respecting employee’s beings and how they want to be
[32:57] How to look at success throughout your career
[37:15] Giving yourself flexibility and grace
[41:05] How to recognize when you’re on the right path
[46:36] Mentors that have made a difference in Elizabeth’s career
[53:58] The ritual Elizabeth does every day for her wellbeing
[56:01] The cuisine Elizabeth is exploring right now
[58:43] The podcasts Elizabeth recommends to the listeners
[1:00:52] The purchase <$100 that has made a difference in Elizabeth’s life
[1:04:15] The final words of advice and inspiration Elizabeth leaves for the audience
[1:05:06] How to contact Elizabeth if you’d like to reach out to say hello


“My gut said, ‘You gotta go be with your mom.’ And I did that, and it was a very, very, very important decision.”

“I had a leader one time who talked about glass balls and rubber balls…you’ve got balls that you’re going to drop and they’re going to bounce, and you’ve got balls that are going to drop and they’re going to break.”

“But what is failure really?It’s something that we, kind of assign a title to without critically [00:28:00] examining what did we learn and how do we take that learning to the next place. So I don’t really think about it as failing. I think about it as, is harvesting knowledge for the next adventure.”

“Success isn’t about the metrics of your job. Success is about, ‘What am I learning? What am I doing that makes me happy, or makes other people successful?”

“I think of mentoring as that you’re intentionally spending time with someone…you’re helping shape and guide someone that you care about, help them on their path.”

“I would tell people that, you know, more than you think you do, you know, to really pay attention to your intuition and when you see a red flag, kind of put that in your memory as a piece of information to kind of use as your overall critical decision making.”





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