Latest / Scrappy but Successful [Consultant's Personalities When No One's Watching] / 31. Stop Building Yourself Another Job: Fractional CXO Company Building with Natalie Hoop

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31. Stop Building Yourself Another Job: Fractional CXO Company Building with Natalie Hoop · Scrappy but Successful [Consultant's Personalities When No One's Watching]

• 0:00
  What's happening, everybody? Welcome to Scrappy But Successful, the show where I sit down
• 0:06
  with your favorite consultants and find out if they're successful because they're sophisticated
• 0:12
  or because they're a little bit scrappy. I'm your host, Jack Tompkins, CEO of Pineapple
• 0:18
  Consulting Firm, always helping small businesses become more data driven.
• 0:23
  Natalie Hoop: So interesting.
• 0:27
  Jack: Today I'm joined by my friend Natalie Hoop. She's a coach for fractionals,
• 0:33
  which given this audience is the perfect guest to have. She's also a fractional COO.
• 0:39
  She wants to help her clients stop building another job and start building a fractional
• 0:45
  business that actually works. Natalie, do you fall more on the sophisticated side
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  or the scrappy side? Where'd you grow up? Did you have entrepreneurs in the family?
• 0:58
  Natalie: Scrappy all the way. Have to be scrappy. I actually grew up in New Jersey,
• 1:04
  that's where I was born and bred. In terms of entrepreneurs, no, I grew up in a family
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  that was a bunch of nurses. My mom was a nurse, my stepdad was an LPN, one of my
• 1:15
  sisters is a nurse practitioner. I'm the black sheep who went into retail, then
• 1:21
  startups, then fractional work, and now coaching.
• 1:44
  Jack: Did you have some innate knowledge of the human body, taking blood, any of those
• 1:51
  baseline things from growing up around medicine?
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  Natalie: What I do have an innate sense of is, when your family is full of medical
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  professionals, dinner conversation is very unique. I am not the person you come to if
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  you're ill, I'll just do a search engine check on symptoms.
• 2:24
  Jack: Does the entrepreneurial piece start early? Lemonade stand, selling cookies as a kid?
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  Natalie: I did the normal after-school jobs, babysitting, convenience store. I actually
• 2:37
  went to school to be a lawyer and realized very quickly law was not for me. I left
• 2:43
  school to figure out what I wanted to do and went into retail. I blame retail for my
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  entrepreneur journey because you learn so much about how everything connects and works
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  together. It served me well in startups and now as a fractional COO.
• 3:34
  Jack: I'd give yourself credit. A lot of people work in retail and learn nothing about
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  how anything works.
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  Natalie: So to tell you scrappy, my first job as a manager was Blockbuster Video. We used
• 3:48
  to create our P&Ls by hand and send them to corporate, which isn't how they do it anymore.
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  You'd have a sheet of paper with all your figures from the previous year, and they'd
• 4:00
  give you a total they wanted you to hit, and you'd have to reverse engineer your labor
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  spend every month with a pencil and a calculator, then fax it to the home office for approval.
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  Very scrappy back then.
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  Jack: How were the grades in school during this early life?
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  Natalie: The grades were really good, I was a straight A student for most of my life.
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  In high school I cared less and we went back to B's, but school came naturally for me.
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  Jack: How about college, good grades there?
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  Natalie: I dropped out the first year. Later I went back and got my bachelor's degree, and
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  by then retail had taught me everything, so it was a breeze. It was online too, which
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  added flexibility. Every time we learned something, I'd already learned it from real
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  life experience.
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  Jack: The more I talk with entrepreneurs, the more I realize on-the-job experience is
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  100% where things are learned. Shout out to the scrappy method of dropping out, learning,
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  and going back for the piece of paper.
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  Natalie: I had a 4.0 and was so proud of myself, but it didn't really benefit me other
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  than the certificate. Real life experience and the training programs companies invested
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  in gave me a skill set more vast than any textbook.
• 7:44
  Jack: Let's go into retail. Are you rising through the ranks, cashier to manager to higher up?
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  Natalie: I started part-time as a cashier at Blockbuster Video. I went to college, left,
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  and was promoted to assistant manager very quickly. I almost became store manager, but
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  they said I was too young. They waited until I hit twenty, then promoted me the week
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  after my birthday. Then I went to store manager, then to Waldenbooks as a seasonal
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  multi-unit manager.
• 9:14
  Jack: So you're at Blockbuster as it's slowly declining and then rapidly declining?
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  Natalie: I was there for three major decisions. The first was DVDs. An assistant manager
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  named Toby came running in excited about this new technology. Our store manager said
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  we'll try it, since back then stores ordered their own copies on a budget. It was a
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  blockbuster, we made so much money and kept expanding. Then corporate came and told us
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  DVDs would never take off and to get rid of them.
• 11:05
  Jack: Were you there for the Netflix thing too?
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  Natalie: Yes, and the third was when we partnered with DirecTV and created Blockbuster
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  cable channels, like five Blockbuster movie channels on DirecTV, to compete with Netflix,
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  because they thought cable beat the DVD mailing system.
• 12:07
  Jack: Were they showing random movies on the cable channel?
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  Natalie: Just movies under licenses, under the Blockbuster umbrella. Part of our store
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  goals were how many satellite dishes and DirecTV customers we could sell because of
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  that partnership.
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  Jack: You're in the weeds at the store level, being data driven about it the old school way.
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  Natalie: They'd gotten burned with laser discs before, so they were very apprehensive
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  about DVDs.
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  Jack: That's an actual boots-on-the-ground perspective most people never hear.
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  Natalie: Want to hear another one? Waldenbooks was bought by Borders, and Borders was
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  approached by Amazon to license borders.com and sell books on it. If you went to
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  borders.com it would transfer you to Amazon. The CEO at the time said no one will ever
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  buy books online, let's make some money off this. A couple years later they tried to
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  take it back, but by then we'd lost all that business to Amazon.
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  Jack: You were so close to becoming a billionaire twice.
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  Natalie: There's a sunk cost fallacy that absolutely exists. In all of those cases,
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  they were so stuck on being right that they never went back, never reevaluated, never
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  pivoted.
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  Jack: Looking back it seems obvious, but at the time it wasn't, right?
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  Natalie: It was obvious. Think about it like AI right now. I'm 100% pro AI, but there's
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  a time and place for it. Companies laying off all customer service to replace it with AI,
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  every one of those reps could tell you it's going to be a disaster. The higher up the
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  lens, the foggier it gets because you're not dealing with the actual users of the product.
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  Jack: Talk to me about reversible decisions. How do you know when to pivot with clients?
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  Natalie: I look at it very much like engineering. Everything can be rolled back. If
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  you deploy something and it breaks three other things, you don't leave it up because
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  of sunk cost, you roll it back and readjust. With business we treat everything as one and
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  done, but new information comes so fast now. You have to figure out why you're making the
• 18:28
  change and how you'll measure it.
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  Jack: Let's use a specific example, like comparing conversion rates on a new sales
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  funnel that's coming in lower. How long do you give it?
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  Natalie: First you have to understand how long the sales cycle is. A three week cycle
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  lets you decide much faster than an eighteen month cycle. You have to give it enough time
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  to go through the cycle once and gather real data before deciding whether to adjust or
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  let it run again.
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  Jack: That's continuous improvement, data-driven. When did you start your fractional practice,
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  and how'd you get your first clients?
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  Natalie: I was laid off in January 2023 and was in panic mode. Someone had posted a
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  fractional job description in a LinkedIn post, not even a formal job posting. I sent a cover
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  letter and resume, never met the guy, and after two meetings he hired me.
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  Jack: How much did you undercharge him?
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  Natalie: I found out three weeks in that I was replacing a fractional program manager
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  who charged three times more than I did. I'd consulted headhunter friends who told me I
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  was asking for too much.
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  Natalie: One of the things I did for them was revamp their entire sales cycle. They
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  had a 238% sales increase in 30 days.
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  Jack: Get lucky once, count it as a win, then go with the tried and true.
• 27:23
  Jack: What's your version of ramen noodle dinners back then? Were you cost-saving anywhere?
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  Natalie: I had severance from being laid off, so I didn't have to ramen noodle it, but I
• 27:29
  went outside of scope and worked way more than I said I would. I was so focused on