Soup-To-Nuts Podcast: Hard learned tips on how to kill it in business without being killed first

By Elizabeth Crawford

- Last updated on GMT

Do you ever feel like you are in mortal combat with your business? Like either you are killing it, and orders are rolling in, sales are up and margins are wide – or it is killing you, and there are packing delays, profits are down and you can’t sleep at night?

If so, you aren’t alone, even though it may feel that way given our culture’s glorification of entrepreneurship and the idealized notion that anyone can successfully build a business from scratch and flawlessly bootstrap it into a $1 billion brand as long as they are willing to go all in.

While inspiring, the price for this fairytale can be high. According to the former CEO of Clif Bar, co-founder of Plum and the current CEO of REBBL Sheryl O’Loughlin, if entrepreneurs are not careful, their singular focus on success could cost them their health and their relationships, which in turn can negatively impact their business.

In O'Loughlin's book, Killing It! An Entrepreneur’s Guide to Keeping Your Head Without Losing Your Heart​ and in this episode of FoodNavigator-USA’s Soup-To-Nuts Podcast, she shares lessons learned the hard way about what it takes to make it in the highly competitive packaged food and beverage industries. These include advice on how to cultivate lasting relationships with other entrepreneurs, family and investors, as well as with yourself and why each of these is essential to an entrepreneur’s and business’ long-term viability.

Separating fact from fiction

“There is a long legacy that we have as entrepreneurs that everything is great,”​ even when it isn’t, because this is how entrepreneurs woo investors and sell their product, O’Loughlin said.

“But at the same time,”​ she added, “We need to get from sales mode to lets-get-real mode. And what we are missing is the lets-get-real mode. And what I mean by that is in a culture where successes are so glorified, there needs to be a place where we can go for admissions like, I am scared, I am really worried, I can’t sleep anymore, I feel like I am falling apart.”

O’Loughlin explains in her book how trying to operate in a world without this safe space made her “literally implode.”​ She added that if she had a “tribe of supporters to help me get through and to relate to the hardships that I was going through,” ​she might have made it “back from the dark side”​ sooner.

Who can you trust in your tribe?

In a world where it seems like no one else is asking for help, it can be difficult for entrepreneurs to find others who can relate to what they are experiencing, help guide them and who won’t use it against them. But O’Loughlin assures they exist. And she says a good place to find them is through old-fashioned networking and professional organizations.

“There are certain people you can have a certain amount of vulnerability with and certain people that you can’t. And it is really important to understand the difference,”​ O’Loughlin said.

She noted many professional organizations and professional friendships come with an expectation of confidentiality, but it is safer to spell it out before sharing too much.

“I will always remember in one of the organizations I was a part of where an executive coach was brought in to work with the senior leadership team and what I ended up finding out what that this person was told as part of their contract to report back to the company as to how it was going with people that is a total violation of trust,”​ she said, adding, “be really clear on who is really an advisor and who really is a coach versus someone who is really at the end of the day going and playing politics.”

Finally, O’Loughlin cautioned entrepreneurs not to forget how helpful friends and family can be.

“Our significant others might not be in the business or understand the specifics of the business, but they understand you as a whole person, and that is what is so important for someone in the depths of despair,”​ she said.

Four traps to avoid when mixing love and work

While friends and family can be just as essential to an entrepreneur’s success as professional relationships, that often have higher stakes and more ways to become damaged unless handled carefully. O’Loughlin outlines in her book four common traps into which entrepreneurs can fall when navigating love and work, and she also give advice on how to avoid them.

The first trap is not sharing buy-in, by which O’Loughlin said she means recognizing that entrepreneurs’ goals impact those they love and therefore their family should have a say in how to achieve those goals.

The second trap is playing the blame-game when things get tough. A better strategy is to skip the blame and work together to find a solution.

The third trap is thinking there isn’t enough time to spend with a life partner or taking them for granted. “If we don’t spend time with our partner, we put our relationship and families and likely our companies at great risk,”​ she said.

And finally, the fourth trap is losing track of your values, which come from shared goals and buy in. Keeping them in front of mind means talking about them and revisiting them regularly, she advised.

Finding the right investor

Entrepreneurs’ relationships with investors can face many of the same challenges as those with significant others, and should be selected and handled with equal care, recommends O'Loughlin. She explained that while the relationship is professional, it often comes with a similar level of emotional and financial commitment and vulnerability as with a life partner.

As such, she said it is vital that entrepreneurs check investors’ references, just like investors are checking their references. Also just like investors, entrepreneurs need to go beyond the list of approved references to call everyone they can think of in order to uncover the bad as well as the good.

Once an entrepreneur has a good investor, they need to trust them and go to them early and often with questions, concerns and achievements so that each can be addressed – or celebrated – in a way that moves the company forward, she added.

Go forward with bold humility

Navigating all these relationships while also managing personal well-being and the logistics of a business could easily frighten potential entrepreneurs away from the idea of launching a new product or company. But, according to O'Loughlin, it doesn’t have to, if the entrepreneur is willing to go forward with what she calls “bold humility.”

Bold humility means being courageous, taking calculated risks and trying new things, but also being willing to ask for help when you get stuck or lost, O’Loughlin said.

“Even though most people believe in traditional business that asking for help is a kiss of death, to me asking for help is one of the most courageous things you can do because that is what can make companies stronger,”​ she said.

O'Loughlin's book, Killing It! An Entrepreneur’s Guide to Keeping Your Head Without Losing Your Heart, ​is packed with many more lessons, and those interested in learning more about book can find it on the publisher’s Harper Collin’s website.

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