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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 April 8, 2019

        22 Tips for Effective Deadlines

        22 Tips for Effective Deadlines

        Unless you’re infinitely rich or prepared to rack up major debt, you need to budget your income. Setting limits on how much you are willing to spend helps control expenses. But what about your time? Do you budget your time or spend it carelessly?

        Deadlines are the chronological equivalent of a budget. By setting aside a portion of time to complete a task, goal or project in advance you avoid over-spending. Deadlines can be helpful but they can also be a source of frustration if set improperly. Here are some tips for making deadlines work:

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        1. Use Parkinson’s Law – Parkinson’s Law states that tasks expand to fill the time given to them. By setting a strict deadline in advance you can cut off this expansion and focus on what is most important.
        2. Timebox – Set small deadlines of 60-90 minutes to work on a specific task. After the time is up you finish. This cuts procrastinating and forces you to use your time wisely.
        3. 80/20 – The Pareto Principle suggests that 80% of the value is contained in 20% of the input. Apply this rule to projects to focus on that critical 20% first and fill out the other 80% if you still have time.
        4. Project VS Deadline – The more flexible your project, the stricter your deadline. If a task has relatively little flexibility in completion a softer deadline will keep you sane. If the task can grow easily, keep a tight deadline to prevent waste.
        5. Break it Down – Any deadline over one day should be broken down into smaller units. Long deadlines fail to motivate if they aren’t applied to manageable units.
        6. Hofstadter’s Law – Basically this law states that it always takes longer than you think. A rule I’ve heard in software development is to double the time you think you need. Then add six months. Be patient and give yourself ample time for complex projects.
        7. Backwards Planning – Set the deadline first and then decide how you will achieve it. This approach is great when choices are abundant and projects could go on indefinitely.
        8. Prototype – If you are attempting something new, test out smaller versions of a project to help you decide on a final deadline. Write a 10 page e-book before your 300 page novel or try to increase your income by 10% before aiming to double it.
        9. Find the Weak Link – Figure out what could ruin your plans and accomplish it first. Knowing the unknown can help you format your deadlines.
        10. No Robot Deadlines – Robots can work without sleep, relaxation or distractions. You aren’t a robot. Don’t schedule your deadline with the expectation you can work sixteen hour days to complete it. Deathmarches aren’t healthy.
        11. Get Feedback – Get a realistic picture from people working with you. Giving impossible deadlines to contractors or employees will only build resentment.
        12. Continuous Planning – If you use a backwards planning model, you need to constantly be updating plans to fit your deadline. This means making cuts, additions or refinements so the project will fit into the expected timeframe.
        13. Mark Excess Baggage – Identify areas of a task or project that will be ignored if time grows short. What e-mails will you have to delete if it takes too long to empty your inbox? What features will your product lack if you need a rapid finish?
        14. Review – For deadlines over a month long take a weekly review to track your progress. This will help you identify methods you can use to speed up work and help you plan more efficiently for the future.
        15. Find Shortcuts – Almost any task or project has shortcuts you can use to save time. Is there a premade library you can use instead of building your own functions? An autoresponder to answer similar e-mails? An expert you can call to help solve a problem?
        16. Churn then Polish – Set a strict deadline for basic completion and then set a more comfortable deadline to enhance and polish afterwards. Often churning out the basics of a task quickly will require no more polishing afterwards than doing it slowly.
        17. Reminders – Post reminders of your deadlines everywhere. Creating a sense of urgency with your deadlines is necessary to keep them from getting pushed aside by distractions.
        18. Forward Planning – Not mutually exclusive with backwards planning, this involves planning the details of a project out before setting a deadline. Great for achieving clarity about what you are trying to accomplish before making arbitrary time limits.
        19. Set a Timer – Get one that beeps. Somehow the countdown of a timer appears more realistic for a ninety minute timebox than just glancing at your clock.
        20. Write them Down – Any deadline over a few hours needs to be written down. Otherwise it is an inclination not a goal. Having written deadlines makes them more tangible than internal decisions alone.
        21. Cheap/Fast/Good – Ben Casnocha in My Start Up Life mentions that you can have only have two of the three. Pick two of the cheap/fast/good dimensions before starting a project to help you prioritize.
        22. Be Patient – Using a deadline may seem to be the complete opposite of patience. But being patient with inflexible tasks is necessary to focus on their completion. The paradox is that the more patient you are, the more you can focus. The more you can focus the quicker the results will come!

        Featured photo credit: Estée Janssens via unsplash.com

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