Entrepreneurs tend to talk about the success, the fun and excitement of running a company. Fewer talk about struggles. Today, on the Unlearn Podcast, Barry O’Reilly talks to Teresa Torres, Product Discovery Coach at Product Talk. They get into what’s hard about the path to success, and at the end of the day, what really matters. Listen to The True Story of Struggles and Success Of A Startup CEO with Teresa Torres.

No One Has All The Answers

Like many young CEOs and founders, Teresa found herself working with people who were older, more experienced, and with access to more resources than she did as a leader. She shares a key unlearn moment about discovering that no one really has all the answers – and how that gave her the confidence to start trying things to see what worked. Barry points out that trying is a learned behavior, and Teresa discusses how education and experience in design-thinking instilled in her the idea that your first attempt won’t always work: iteration is the key to achieving your goals. [Listen from 3:45]



A Process for Decision-Making

Very little about being a CEO is black and white – and coming from an environment where situations were more granular was a challenge for Teresa. She says sales is a lot like product development, and gives us some insight on the similarities, and how she brought an outcome-based focus into her work as a product leader and later as a CEO. Every process has parts, and those parts can be modeled, measured and optimized. [Listen from 7:25]

Our Defaults Can Be Unhelpful

When people are working under stress, they tend to revert to the skills, strategies, and habits that they are the best at – it feels good, and more importantly, it feels productive. Barry and Teresa talk about how this tendency can actually work against people whose roles are less about producing, and more about helping other people produce, or taking a bigger picture view of the growth and direction of a company. This is especially challenging when every situation feels extremely high stakes. [Listen from 12:00]

Letting Other People Help You

Teresa recalls the scenario her company was navigating through during the economic downturn, and how critical it was to let her team play to their own strengths and be responsible for their outcomes – and importantly, create a space for them to be transparent with her about her work and responsibilities. During a particularly fraught time, Teresa wasn’t going to make payroll and ended up offering team members the option to become owners in the company. This had several beneficial outcomes and ended up giving her employees a unique learning experience, as well as company stock. [Listen from 21:25]

Defining Success on Multiple Levels

After being a CEO, Teresa had to decide what came next. She experimented with different projects and determined that what she wanted to tackle was the waste of time and talent endemic in many startups, founding a new company to do so—Product Talk. Barry brings up how, as a solopreneur, it can be difficult to handle loss-aversion, and constantly feeling like you have to take every opportunity that comes along. Teresa’s answer to this is to try and make sure you have only awesome options to choose from and shares some examples of how she’s made that a part of her working life. [Listen from 25:00]

What Feels Fun That Helps?

Teresa used what she calls a divergent-convergent process to try many different options to help weed out what she didn’t want to do. Barry and she discuss how this applies to both business and to life, and why embracing an abundance mindset can help you identify and create many amazing options for yourself—therefore improving the options you end up selecting to succeed. [Listen from 30:30]

Start Your Unlearning Journey

Unlearn: Let Go of Past Success to Achieve Extraordinary Results by Barry O’Reilly

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