Lori Osterberg – Co-founder of VisionOfSuccess.com

Try and test. I’m willing to try all kinds of marketing ideas, as long as they fit within my demographics. I have learned some amazing things by being open and willing to try things. Yet I also know how to test to make sure they work at an acceptable level.

Lori Osterberg is the co-founder of VisionOfSuccess.com, a website and coaching business helping 40-60 something women reinvent their lives as an entrepreneur, offering advice and helping them take their big ideas to the six figure level and beyond.

Reinvention is something Lori knows well. She started after college down the 9 to 5 path, only to question it all when her 54 year old father died from a massive heart attack. After watching him struggle for years, re-interviewing again and again for a job he didn’t like, hoping to hang on for his retirement check, she knew there had to be a better way. With what she learned, she knew escaping the 9 to 5 was critical, and quickly jumped in with both feet to the entrepreneurial lifestyle.

Today’s she’s a serial entrepreneur with several businesses behind her. Two years ago as her daughter was transitioning from high school to college, Lori felt the need for reinvention once again. This Denver native sold off her house, two-thirds of her belongings, and her then-business, all for the desire to see more of the world. She created VisionOfSuccess.com to help others reinvent themselves, all the while documenting her own journey as a living example. She’s currently living for one year in the Pacific Northwest, exploring Canada and the Northern States.

Where did the idea for VisionOfSuccess.com come from?

I was at a networking event. I spent some time telling a woman about my adventures as an entrepreneur, what it was like starting up several businesses, writing books, coaching – all the things I’ve done in my career condensed into a 60 second overview. I then asked her if she liked what she did. “No, but it pays the bills” is how she answered. She then launched into a several minute story about her true desire of writing a book and starting a coaching business to help other families get through the medical trauma she had experienced with her own son after he was born.

We went back and forth for a while, and I gave her solid advice on steps she could take to begin writing her book, developing her coaching practice, and moving forward with her dream of developing a business. That conversation motivated me to sell off my existing business and start up VisionOfSuccess.com to help women reinvent themselves as business owners as a part of their second act.

What does your typical day look like and how do you make it productive?

I rise at 5:30 to meditate, do yoga, and write. We rented a home along the river, so I spend an hour or so walking along it mid-morning, enjoying all of the new sights and sounds. I work via Skype and phone in the afternoon for coaching and more writing, depending on what project I’m in the middle of. And we spend every weekend exploring a new region.

I am very clear on what needs to get done. Because exploring is as important to my life now as working, I make sure I keep very clear goals and to-do lists to keep me on track. I look for efficiencies wherever possible. I question how important things are all the time, and eliminate things that are more busy work then anything else.

How do you bring ideas to life?

I like vision boarding everything I do. When I have an idea, the first thing I do is make sure it fits in with my long term vision. I’m an idea person, and can come up with a lot of ideas all the time. So first I make sure it aligns with my ultimate goals. If it passes that test, then I vision board out how the concept will fit in, and what the final product/service looks like. The clearer I can see it, the easier it becomes to bring it to life.

What’s one trend that really excites you?

Crowdfunding! I’ve attended quite a few seminars and meetups on crowdfunding, and have invested in a few interesting things I’ve found through Kickstarter and a few other sites. I developed a book campaign for Pubslush (a book publishing crowdfunding site) a year ago that failed to be funded, but I simply look at that as a stepping-stone. I’ll be trying that one again soon. I also attended a meetup and met the owner of the highest funded Kickstarter campaign to date, the Coolest Cooler, which furthered my interest in this concept. I know this is the future of financing small business, and I’m excited to learn as much as I can.

What is one habit of yours that makes you more productive as an entrepreneur?

Before I tackle any project, I always ask if it’s the best use of my time, and if it applies directly to my ultimate goal. Simply asking “How will this help me?” has helped me avoid doing a lot of things that simply would be fluff work, and wouldn’t get me the results that will make the most impact on what I’m trying to accomplish.

What was the worst job you ever had and what did you learn from it?

The worst job I had was actually a high paying, high ranking auditing position I had right before I became an entrepreneur for the first time. I took it because of its potential, but quickly learned the management team were micromanagers. I couldn’t write a report correctly; my boss would change every detail no matter how much effort I put into it. We would sit around for weeks with nothing to do, waiting for management to finalize pieces of the project. The biggest lesson was that there had to be a better way! It gave me all the push I needed to give the entrepreneurial world a try.

If you were to start again, what would you do differently?

The first thing I would do is hand over more of the details to a support staff. I would hire virtual assistants at a greater speed, and allow others to help me grow at a faster pace.

The other thing would be to jump in and start attending seminars, training programs, and other events that would put me with like-minded people. Connections are everything; and the quickest way to make them is by attending events where they congregate heavily together.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

It may sound simple, but my answer is read. Read everything you can get your hands on. Read books that make the top sellers list. Read biographies on the top business people. Look for recommendations from friends and acquaintances on your social sites. I try to read at least one book a week, and it opens up my mind to unlimited potential.

What is one strategy that has helped you grow your business? Please explain how.

Try and test. I’m willing to try all kinds of marketing ideas, as long as they fit within my demographics. I have learned some amazing things by being open and willing to try things. Yet I also know how to test to make sure they work at an acceptable level.

What is one failure you had as an entrepreneur, and how did you overcome it?

Having my first employee quit. I knew it was coming; I knew she wasn’t happy. And I knew it was mostly my fault, because we didn’t establish a clear job description and changed our business focus all the time. It taught me to be much clearer when I hire someone for a job, and to make sure I have the right guidelines in place.

What is one business idea that you’re willing to give away to our readers?

An easier way to give exposure to booths at farmers markets. Here in the Pacific Northwest, we hit farmers markets all the time, and I always find myself wondering what the name of that little booth on the corner was. You can usually find the farmers market online, but they don’t do much to promote the little guys that may only come a few times a year.

What is the best $100 you recently spent? What and why?

A one day trip to Mt St Helens to tour the Ape Caves. The Ape Caves are the longest continuous lava tubes in the US. They are simply amazing – just make sure you have great hiking shoes and a very bright lantern.

What software and web services do you use? What do you love about them?

I write all the time, and couldn’t live without Scrivener. It’s the best at keeping your thoughts organized, and allowing you to divide your work into workable sections.

I also love Wave. It’s a great online accounting and invoicing system, and the best part is it’s free! It’s perfect for small businesses that don’t use payroll and like to keep things easy.

What is the one book that you recommend our community should read and why?

One of my current favorites is Bold by Peter Diamandis and Steven Kotler. It’s a great future thinking book that provides a lot of insight into how the world is changing in the coming years, and what you can do as an entrepreneur to keep up.

What people have influenced your thinking and might be of interest to others?

James Altucher is an amazing writer and entrepreneur and has provided me with a lot of motivation lately.

Sandy Franks runs the Women’s Financial Alliance and puts out an informative newsletter filled with advice.


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Lori Osterberg on Twitter: @LoriOsterberg
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