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The Era of the Unintentional Entrepreneur: An Interview with Kevin Reeth of Outright.com (Part 1)

The Era of the Unintentional Entrepreneur: An Interview with Kevin Reeth of Outright.com (Part 1)

The Era of the Unintentional Entrepreneur

    With a background including successful stints with Yahoo, eGroups, and Intuit, Kevin Reeth was well-prepared to strike out on his own as a co-founder and CEO of the web start-up Outright.com, a free online bookkeeping platform for small businesses and self-employed persons. In today’s economic climate, though, more and more people are finding themselves thrown into entrepreneurship without a background like Reeth’s as their companies fold or downsize leaving them to strike out on their own.

    To help these “unintentional entrepreneurs” get their feet under them, Reeth partnered with Network Solutions to form Unintentional Entrepreneur, a website and organization dedicated to helping newly self-employed workers get off on the right foot as freelancers, consultants, and small business owners. So far, Unintentional Entrepreneur has hosted free seminars in a handful of cities, with more on the way, combining formal presentations with social networking in an effort to provide the information and social environment fledgling entrepreneurs need to start building towards success.

    After I wrote about Outright.com at Freelance Switch and on my own site, The Writer’s Technology Companion, several people at Outright.com contacted me and struck up a conversation, culminating in an offer to interview Reeth about Unintentional Entrepreneur and the challenges – and rewards – facing today’s entrepreneurs, unintentional or otherwise.

    This is part 1 of a three-part series. In this section, Reeth and I discuss entrepreneurship in general. In part 2, we’ll discuss the way that technology is changing the entrepreneurial landscape, and in part 3 what Unintentional Entrepreneur is doing to help first-time self-employed workers. The interview was conducted on July 17, just after their first event in Los Angeles.

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      Dustin Wax (DW): Let’s start with a general question: What is an unintentional entrepreneur?

      Kevin Reeth
        Kevin Reeth (KR):

        An awful lot of our customers are folks who were working in corporate America and had had paying jobs for years and had lost their job last fall or early this year, had been looking for a job, and had gotten to the point where they had to figure out something to do. And now they’re starting to hang out their own shingle to see if they can earn a living that way.

        What’s interesting is, compare them to people who’ve been small business owners or self-employed for many years, who had gotten used to it. People leaving the confines of a corporate job quickly get a pretty significant wake-up call in terms of what it means to work for yourself.

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        DW: So you have the wave of people for whom entrepreneurship has become an only option, something that came onto their radar as an option not because of an internal drive to do it but because of the economy.

        KR: Yes, I think that’s exactly right. This may not have been something that they thought about, maybe they never did have that drive, maybe they weren’t maybe wired that way or maybe they’re more risk-averse. But now they have certain practical realities that are forcing them to consider new options, and entrepreneurship is one of the options they’re considering. And so, they may have never done this before and may not understand what it means to operate as a business right now.

        DW: What does it mean?

        KR: The first focus, honestly, needs to be sales. If you don’t have people paying you, nothing else matters. You’re not going to be a very successful business for long.

        Along with that, when you first get started, it’s all about networking. Your initial business is going to come through referrals, friends and family, and coworkers and associates. It’s not going to be through advertising and promotions, and not from fancy marketing stuff. By getting out there and getting connected to people, you will have opportunities present themselves.

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        And then where we tend to focus, where Outright focuses is on helping people understand that they need to prioritize their time, that time is going to be their most precious commodity. There’s a lot of stuff you can do dirt cheap or free, but one of the worst things you can do is get bogged down in the details of stuff that really doesn’t matter. Use technology where it can be most effective. Automate the stuff that doesn’t provide value, and doesn’t grow your business. Honestly, the back office stuff, the bookkeeping – we know it’s not sexy. This is not what you want to be spending your time doing. Use the technology available to automate that, so you can be out there, doing sales, servicing existing customers, getting more repeat business, not worrying about where the money is going, whether something is deductable or not, remembering to pay taxes on time.

        DW: You said that the first focus is sales. There’s a skill set involved in sales, though, that very few people have. If you’re an engineering person or computer scientist or whatever, how can you develop or sharpen those sales skills?

        KR: I think that’s actually more daunting than it has to be. People tend to think about it as, “OK, I have to go do sales, I have to sell myself.” And the secret with networking is that, if you go out there and just meet other people, you understand that all of us are in the same boat at the end of the day, all of us need help. It’s all just building relationships.Even at the big enterprise sales level, so much of sales comes down to whether people like each other, whether they get along, and whether they have a relationship. There is a bias in decision-making around purchases that goes beyond just the rational facts. So you don’t have to be the greatest salesperson in the world, you just need to be able to build relationships with people.

        DW: We’ve talked about the challenges facing new entrepreneurs, but what are some of the benefits of being an entrepreneur, especially in today’s economy?

        KR: One, I think it will become one of the most empowering experiences you can ever have. It’s one of those things where it is a personal journey for anybody who tries it. A lot of things are going to go wrong. You’re going to fail at a lot of things. But you’re going to learn an awful lot about yourself. You’re going to find out what you’re capable of, and that’s invaluable.

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        Another great thing is that you will extend your network dramatically. You are going to get to meet so many new and interesting people that no matter what the future holds, you’re going to build relationships that are going to last.

        And there’s the education component. You’re going to be forced to learn more in the first three months working for yourself than in years working for someone else. And at the end of it, you will have that knowledge, you will have that experience. It’s going to make you better not only working for yourself but if you ever go back and work for someone else, you’re going to be significantly better at it.

        These are not easy things, they’re not free, awesome things that just happen to you, you have to work for them. But the value you get out of that journey is immense.

        In Part 2 of this series, we’ll discuss some of the ways technology is changing today’s small business and self-employment landscape, and the tools that Reeth recommends for new entrepreneurs. See you then!

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        Last Updated on August 16, 2018

        The Importance of Reminders (And How to Make a Reminder That Works)

        The Importance of Reminders (And How to Make a Reminder That Works)

        No matter how well you set up your todo list and calendar, you aren’t going to get things done unless you have a reliable way of reminding yourself to actually do them.

        Anyone who’s spent an hour writing up the perfect grocery list only to realize at the store that they forgot to bring the list understands the importance of reminders.

        Reminders of some sort or another are what turn a collection of paper goods or web services into what David Allen calls a “trusted system”.

        A lot of people resist getting better organized. No matter what kind of chaotic mess, their lives are on a day-to-day basis because they know themselves well enough to know that there’s after all that work they’ll probably forget to take their lists with them when it matters most.

        Fortunately, there are ways to make sure we remember to check our lists — and to remember to do the things we need to do, whether they’re on a list or not.

        In most cases, we need a lot of pushing at first, for example by making a reminder, but eventually we build up enough momentum that doing what needs doing becomes a habit — not an exception.

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        The power of habit

        A habit is any act we engage in automatically without thinking about it.

        For example, when you brush your teeth, you don’t have to think about every single step from start to finish; once you stagger up to the sink, habit takes over (and, really, habit got you to the sink in the first place) and you find yourself putting toothpaste on your toothbrush, putting the toothbrush in your mouth (and never your ear!), spitting, rinsing, and so on without any conscious effort at all.

        This is a good thing because if you’re anything like me, you’re not even capable of conscious thought when you’re brushing your teeth.

        The good news is you already have a whole set of productivity habits you’ve built up over the course of your life. The bad news is, a lot of them aren’t very good habits.

        That quick game Frogger to “loosen you up” before you get working, that always ends up being six hours of Frogger –– that’s a habit. And as you know, habits like that can be hard to break — which is one of the reasons why habits are so important in the first place.

        Once you’ve replaced an unproductive habit with a more productive one, the new habit will be just as hard to break as the old one was. Getting there, though, can be a chore!

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        The old saw about anything you do for 21 days becoming a habit has been pretty much discredited, but there is a kernel of truth there — anything you do long enough becomes an ingrained behavior, a habit. Some people pick up habits quickly, others over a longer time span, but eventually, the behaviors become automatic.

        Building productive habits, then, is a matter of repeating a desired behavior over a long enough period of time that you start doing it without thinking.

        But how do you remember to do that? And what about the things that don’t need to be habits — the one-off events, like taking your paycheck stubs to your mortgage banker or making a particular phone call?

        The trick to reminding yourself often enough for something to become a habit, or just that one time that you need to do something, is to interrupt yourself in some way in a way that triggers the desired behavior.

        The wonderful thing about triggers (reminders)

        A trigger is anything that you put “in your way” to remind you to do something. The best triggers are related in some way to the behavior you want to produce.

        For instance, if you want to remember to take something to work that you wouldn’t normally take, you might place it in front of the door so you have to pick it up to get out of your house.

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        But anything that catches your attention and reminds you to do something can be a trigger. An alarm clock or kitchen timer is a perfect example — when the bell rings, you know to wake up or take the quiche out of the oven. (Hopefully you remember which trigger goes with which behavior!)

        If you want to instill a habit, the thing to do is to place a trigger in your path to remind you to do whatever it is you’re trying to make into a habit — and keep it there until you realize that you’ve already done the thing it’s supposed to remind you of.

        For instance, a post-it saying “count your calories” placed on the refrigerator door (or maybe on your favorite sugary snack itself)  can help you remember that you’re supposed to be cutting back — until one day you realize that you don’t need to be reminded anymore.

        These triggers all require a lot of forethought, though — you have to remember that you need to remember something in the first place.

        For a lot of tasks, the best reminder is one that’s completely automated — you set it up and then forget about it, trusting the trigger to pop up when you need it.

        How to make a reminder works for you

        Computers and ubiquity of mobile Internet-connected devices make it possible to set up automatic triggers for just about anything.

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        Desktop software like Outlook will pop up reminders on your desktop screen, and most online services go an extra step and send reminders via email or SMS text message — just the thing to keep you on track. Sandy, for example, just does automatic reminders.

        Automated reminders can help you build habits — but it can also help you remember things that are too important to be trusted even to habit. Diabetics who need to take their insulin, HIV patients whose medication must be taken at an exact time in a precise order, phone calls that have to be made exactly on time, and other crucial events require triggers even when the habit is already in place.

        My advice is to set reminders for just about everything — have them sent to your mobile phone in some way (either through a built-in calendar or an online service that sends updates) so you never have to think about it — and never have to worry about forgetting.

        Your weekly review is a good time to enter new reminders for the coming weeks or months. I simply don’t want to think about what I’m supposed to be doing; I want to be reminded so I can think just about actually doing it.

        I tend to use my calendar for reminders, mostly, though I do like Sandy quite a bit.

        Featured photo credit: Unsplash via unsplash.com

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