This is Find Your Dream Job, a podcast that helps you get hired, have the career you want and make a difference in life.
I am Mac Prichard, your host and publisher of Mac’s List. Our show is brought to you by Mac’s List and our book, “Land your dream job in Portland and Beyond.” To learn more about the book and the updated edition that we’re publishing in February, visit macslist.org/ebook.
Thanks for joining us today. This week on Find your dream job, we’re talking about how to be a founder. Have you ever thought about striking out on your own? Maybe you want to start a non-profit or a private company or a consultant practice. Whichever option you chose, you need to think carefully about the road ahead. Being a founder offers many advantages but you need to be clear about why you want to do it and understand what it takes to succeed.
Our expert desk this week, Russ Finkelstein has helped start two organizations. One was quite successful, the other one failed and now he’s part of a third start-up. Later in the show, Russ will share his story and his dos and don’ts for founders.
But maybe you don’t want to start your own organization. Maybe you want to be a solopreneur, a one-person start-up. Ben Forstag will join us and he’ll discuss a book and resources you can use to launch your own venture for $100 or less. Cecilia Bianco, as she does every week, answers our listeners’ question and this week, she’ll share with you five key questions you need to answer before you leave your day job and start your own show.
So how about you two, have you ever thought … Ben and Cecilia about after Mac’s list perhaps starting your own organization?
I don’t know if that would be the right thought for me, seeing all the different blogs and articles we see about it. I just think I’m not ready for all that risk. I can’t think about it yet.
Okay. You think about the risks that’s involved. Yeah, I can sympathize. And Ben?
I want to work for you forever Mac! No, I fantasize sometimes about starting my own business but there are a lot of risks there and at this point of my life, I’m not quite ready to take those risks.
I’ll share with you. I’ve been self-employed now for eight years and when I first started out on my own, I had a day job that kept me busy half-time and then the other half, I was running my public relations company, [inaudible 00:02:30] Communications. People would say to me in those days, “How does it feel?” And I would say, “It’s like standing on a dock and you got one foot in a row-boat and it’s slowly drifting away from the dock and I’ve the other foot on the dock and I can’t decide where I should shift my weight,” and eventually I chose the boat and here we are, eight years later.
Thanks for making that decision.
It’s great to be here.
Ben, let’s take it back to you. I know you have a resource of the week you want to share with us? What have you discovered for us this week?
Since we’re talking this week about going out on our own and doing your own things, starting your own business, being your own boss, I thought this would be a good time to talk about Chris Guillebeau Portland-based entrepreneur, business writer and motivational speaker.
Chris is a really interesting guy. By his own admission, he’s never held a regular job. Instead he is consistently found ways to turn his ideas into income, so that he can avoid the regular 9-5 lifestyle. What his real passion is, in addition to business is travel and he probably talks about and writes about how he’s been to all 175 countries on earth all before the age of 34.
So my resource this week is actually going to be Chris’ website which is chrisguillebeau.com. His last name is French, as you might be able to tell and that’s spelled Guillebeau and I’ll have the URL in the show notes. His website is the place where you can access all of his products that he makes available. He’s got a blog where he talks a lot about work productivity. To some extent he is a what they might call a productivity ninja about how you can be more effective with email and in working in your office, working in your own business and other writers contribute to his blog as well and write about the same thing and almost everyone there … the way they support this lifestyle is through their own start-up companies and they’re all solo entrepreneurs.
Chris also has written several books. A lot of them are pretty well known. Mac referenced one earlier, it’s called “The Hundred Dollar Start-Up,” and this outlines a general business model for how you can start your own business starting with a blog around a very focused subject and building off from that. He also wrote a book called, “The Art of Non-Conformity: How to live on your own terms by exploring creative self-employment for radical goal setting, contrary in travel and embracing life a constant adventure,” and a third book, this one I’ve actually not heard of. It seems interesting. It’s called “Born for this: How to find the work you meant to do.”
All these books are available on his website and you can check him out there. He also coordinates several big events and I know, Mac you’ve been to some of these and Cecilia and I just got back from one. He hosts one called “Pioneer Nation” which is focused around small businesses and improving how you do things, how you launch, how you market yourself. Cecilia and I went to this about a month ago, got a lot of good stuff out of it. Then he has one of the best named events I have ever heard called, “World Domination Summit” every year. I’ve not being to that one. I know you have Mac.
Can you talk a little bit about it?
I have been twice and it takes place over a weekend and there are both speakers who talked to a large group and smaller sessions as well and it’s very inspirational. I think it offers a lot of benefits. The two that stand out for me are that it provides a weekend that helps you get to think about your goals and purpose in life and where you want to go and provides some ideas about how to get there. Then the second benefit is the community that it brings together and I’ve stayed connected as many people have who have attended World Domination Summit with what other people call themselves WDSers and they’ve had some good friendships and good professional relationships come out of both of those.
Yeah, and one of the recurring themes throughout the events and the books and the blog and this is something we’ve talked a lot about on our podcast here is really getting focused and knowing what you want to do, what you want to deliver and why you want to want to deliver it. Getting to why is what they talk about a lot.
So, his website, chrisguillebeau.com is really the portal to the books, the blog and the events and I’d suggest our listeners to check it out. I’ll have the URL in the shout outs.
Okay. Thank you Ben. Let’s turn to Cecilia. Cecilia is our community manager and she joins us every week to answer you questions. What do you have for us this week Cecilia?
Our question today is, I’m thinking about self-employment but not sure if I’m ready. What are the big issues I should consider to make my decision?
First off Mac obviously has a lot more insight into this question as a business owner but I’ll give my best answer and then we can hear your input Mac.
In my opinion, you need to start by asking yourself these five questions to determine if your really ready.
- Do you know what you want to do and who you want to serve?
- Do you know what your main source of income will be and have a plan in place to effectively promote and sell it?
- Do you have a support system of professional contacts, mentors, family, friends and other resources to help you as you get on your feet?
- Are you prepared to take on the risks associated with running your own business? Clearly I mentioned earlier, I am definitely not.
Lastly, do you have a backup plan or financial cushion should your business fail?
Mac, how did I do? Did I miss any big issues?
I think this is a great list and I think you had almost all the main points. One thing I wrestled with is when I was going through this process was mindset. I had always worked for other people and I never saw myself as an entrepreneur and I think in the popular culture, people think business owners are people who are kind of born into it, maybe they have a family that runs a small business or they are going to Silicon Valley and they’re going to start a tech company.
I think I would challenge our listeners just to think about experiences they’ve had in their careers where perhaps they’ve organized events or helped a non-profit keep going or they’ve involved in school groups and those all require entrepreneurial skills and when people think of themselves in that light, I think it makes it easier for them to make that leap.
In my case … I think I’ve talked to both of you about this. I have been involved in a lot of political campaigns over the years … Electoral politics is a passion of mine and a campaign is the ultimate start-up because it takes place over a short period of time and requires investors and there is the product, the candidate and you know on election day whether or not you have a sale. That would be the only thing I’d add is mainly a mindset.
Okay, great. Each of these questions, they take a lot of thought and planning to address but once you do, I think you’ll have a clear path forward and be able to see if your mindset is in the right place as you mentioned.
One last thing, there’s also a ton of resources out there to help you as you think through these things and today you mentioned a great book and two amazing events that are great examples of ways to get help figuring it all out, so looking for those opportunities in huge before you get started and if it’s possible, talking to people like Mac and other entrepreneurs and business owners and seeing how they got started, what problems they encountered and things they wish they would have know before jumping in is a great way to evaluate yourself from hearing about their experience.
Mac, Ben, anything to add?
I would just go back to what I mentioned two minutes ago which is really getting to the question of why. Why are you doing this. One reason for any entrepreneur is going to be income. They need to pay rent and they want to take care of their family but hopefully there is some bigger why behind it animates what you do and the clearer you are about why you are doing this and why you are taking this road less traveled, that’s really going to give you the guidance you need when you have a rough patch in your business or when you’re struggling. That’s going to provide you clarity and inspiration moving forward.
I think that’s spot-on Ben.
Thank you Cecilia. If you have a question for Cecilia, you can email her. Our email address is email@example.com. The segments by Ben and Cecilia are sponsored by the 2016 edition of Land Your Dream Job in Portland and Beyond. We’re making the complete Mac’s list guide even better by adding new content and making the book available on multiple e-reader platforms.
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Now it’s time to hear from our expert guest. Joining us this week is Russel Finkelstein who is managing director of Clearly Next which helps people of all incomes build life-long fulfilling careers. He is also a senior advisor to Tel Misanthropy which increases investment by funders in the non-profit and social change work force. Russ serves on the national board of the young non-profit professionals network and he was a founder and associate director of idealist.org.
Russ, thanks for joining us.
Thanks for having me. I’m very impressive on paper. Glad to chat with you.
Yeah, it’s a pleasure to have you here. So, starting your own gig. Let’s talk about that.
What should people think about? Whether they want to create a non-profit or perhaps a consulting practice or a private company.
I think I always start with the reasons why people want to begin something. I think very often people when they are thinking about making any kind of transition, there is a lack of clarity as to the rational for why they want to do that. So very often someone is like, “I have got the worst boss and I’m going to go and I’m going to make … I’m sick of having bosses because all bosses are awful. I’m going to go to some other place and start up my own thing and life is going to be easier and plentiful. I’ll have my own schedule.”
I think there is a notion that … sort of a simplistic notion that that’s going to happen. I think the starting point is understanding, one, why you want to do it and then given that, what’s the reality of making that kind of transition.
So don’t flee from something. Actually be working towards something.
Yeah. You have to do your best not to be reactive. It’s being proactive to stuff that’s taking place in your life, in the given workplace but also understand the kind of lifestyle that you want and how it connects to what it would mean to start-up another endeavor.
Okay. So you’ve been through this process several times now. What are common steps that worked for you that listeners should consider taking as they think through whether or not they should strike out on their own?
One of the first things, it just comes down to research. It just whatever the en devour is, whether it’s in the non-profit sector or consulting or for profit. It’s understanding what the void is, what is the thing that you are going to fill. Are you credibly in a position to go and fill that? How easy is it to develop business? How risk averse are you around having to be a rainmaker.
A lot of it is really doing internal work to understand what you want and then the other thing because we do wonderful jobs we’d be lying to ourselves. Like we are an amazing at lying. One of the things when I was working on the start-up that didn’t go … one of the things that’s I’ve always told myself is that, if you work hard enough you can work through anything. And it was one of those things where I reached at a point where I realized with all your possibilities which was the start-up that I hated working on my own. I felt very isolated and even though I had advisors. One thing I would always recommend to people is, have a conversation with people you trust. I always call them people of standing which are people that you communicate well with, you trust and you’re not going to be dismissive of. Very often we reach out to people that we’re comfortable with, so our parents, our partners, our best friends, sibling … but it’s also very easy for us to dismiss that and dismiss their opinions.
That for me is a really important thing and even in the start-up mode, I had some people that I trusted but I realized actually more than just checking things out and having them vet for me, I had to feel like someone was all in the way that I was. It was just hard for me to do that and I had to learn that.
So first get clear about the void or the problem. The void you’re filling, the problem you’re solving but then be clear about what you want out of the experience and turn to trusted advisors to help you think that through.
Yeah. The people who know you best who can push both on your ideas and can give you real feedback on how sustainable those ideas are and then given what they know of you, how realistic it is for you to be that person moving ahead.
How do you find those people Russ? Are these co-workers or … Obviously they’re probably people already in your life or maybe they’re not.
What have you seen work well and not wanted for yourself but for others in both identifying these trusted advisors and then building a relationship with them?
Sure, I think people get hung up on this awful word known as mentor. My least favorite words because people have this notion that there is going to be this one person that has all the answers for everything and that they’re going to make an official request of someone to be their mentor and they will sit at their feet and learn everything.
In fact what happens is, in life you interact with who have expertise on specific things that you might need … instead of thinking about one person giving you feedback, it’s just really thinking back on the people that you’ve worked with who have built a relationship with, who trust you that you communicate well with and they may not be able to give you feedback on the totality of something, but they can give you the feedback on pieces of it.
There is a woman I’m working with in Chicago who is working on a start-up and when we’ve chat about it, she’s classic case of the great cutting away of the good. The challenge of I’m afraid of sharing a thing for fear that it might be good enough. With her, I’ve mentioned a couple of people that she can start with. Like two people who are safe people who are really smart so she can feel really comfortable that, one if they’ve read through something, it’s likely to have been well vetted and two, the other challenge a lot of people have is who are they to do this thing. Who am I to be the founder of this thing. In fact that’s going to come up later on when it’s time for funding or other kinds of support, that who are you will certainly come up.
But initially, I think very often when people struggle with that, one of the things that I will often tell people about is, think about your friends, think about those people that you really respect and you know that those individuals can chose who they are going to spend time with, who they are going to make themselves available to and if you respect and think highly of those people, then that in itself as a sign that you are onto something, that you are someone who has merit in the world, your ideas have merit in the world and sometimes it’s just sort of the latter of confidence and you’ve got to build a solid initial foundation of sharing with a couple of people and kind of build from there.
You touched on this. I think some people think a mentorship has to be a formal relationship with an agreement or regular meetings and I’ve certainly been approached and I know you are often with people who have a specific question about a particular problem and I might not hear from those folks again for months or maybe even several years but I feel good about having that conversation because they’ve approached me about something I can actually help them with.
And even as a mentor … There is a gentleman I work with who graduated from MIT early and therefore bright and is working on something that I barely understand. Like I can get maybe 30% of what he’s talking about but I can help him with the structure of what he’s doing. His ability to get your toaster and your refrigerator talking to one another is completely beyond anything I’ll ever be able to grasp but I understand what he needs to move this thing ahead and to feel confident about it and to prioritize things.
So it really is just to understand that different people have different traits but also that he and I communicate really well in terms of process.
Who shouldn’t be a founder? Are there people that should just take themselves out of the running right from the start?
I don’t know that there is anybody who shouldn’t ever be a founder. I think that it’s just a question of understanding the reality. So if you’re somebody who for example, doesn’t want to ever have to deal with raising money, getting clients any of the associated things that are involved with being a founder, that’s going to be difficult.
Maybe you look into co-founder-ship which is a whole other thing given your skill-set. I think you have to ask yourself how comfortable I am playing the kinds of roles that are necessary for that work and just again be really clear about the lifestyle because if someone could decide that I’m going to begin my own consultancy and say, “Okay. I’m going to keep my job. I’m going to do it on the side.” Some things are slow build and some things require you to be all in very early on. I think it depends on the nature of that thing and what again, I keep using this lifestyle word but what’s you’re mortgage like. How you’re taking care of … you have a family to deal with. What does that take care of in terms of your hours, what does your partner do if you have one in terms of dealing with the bill.
A lot of this stuff involves a lot of other relationships and you’re making very specific choices. There was a start-up that we never have mentioned to you. When I was an idealist in the first five or six years into idealist I had been thinking about an idea that since nothing has ever really happened with it. I’m never going to do it. It was in New York City and it was developing something that would be for LGBTQ non-profits.
It was going to be an organization that both built the capacity of the organizations and also run as a volunteer center within that community. I was interested in it and I spoke with people who wanted to be on the board and I was able to do some perspective fund raising and then I got to the point … I got to the tipping point of defining, am I going to go and be that person or not and I decided do I want that to be who I am, Do I want to be the person who is in front of the cameras, who is doing interviews and that shapes who I want to be in terms of a public person.
Even now with Clearly Next, I’m at a moment where I’m doing this podcast but by large, my preference is a lot of one to one conversation of working with founders, to build big things. I love one to one career conversations but I’m not necessarily the guy who’s looking to be the big public speaker. I’m not necessarily somebody who wants to go and have to be heavily published and I’m in a moment where I probably going to have to start doing that which makes me a little bit uncomfortable but I’m working through it. Actually you can see by virtue of my speaking into this microphone.
Okay. It’s good to have you work through that and I’m intrigued by your point earlier about co-founders. When does it make sense to invite co-founders and what do you look for when you’re doing that?
It is so messy. I think the challenge is distrust. The challenge is if you use someone who … If there are two people who have come together, who organically have developed in that way, I think that’s fine. But if you use someone who is taking a running start at something and you’ve said, “You know what, I need to have someone with more technical jobs, programming jobs.”
Very often you’ll see there is an idea person who is maybe comfortable with sort of fund-raising and some elements, I really need to have someone who can code or can do certain types of tech and those kinds of people are very difficult to find because they are very much in demand. But I’d say that the challenge is an equal report in interest in the work itself and developing the trust.
Like early on, with Idealist for example, I remember maybe the first six to nine months in, I had a conversation with Amy and I said … So my thing is no one will ever work harder than me. I don’t ever like it when anyone is working harder than me at any project. We would work from 8AM till 2AM many night during the initial phase of idealist and somewhere I said, “I need you to share power more because I can’t continue working this hard and not feel like I have ownership.”
I think it can be really challenging for people on the ownership side and depends on the personality of the person who is founding and what they’re founding but I think the trust thing that was really huge. There isn’t one place to find it. There isn’t sites like founder dating or other kinds of sites but it really is, there is a level of trust there and I’ve known lots of guys speak to founders all the time and that challenge of trust and a lot of people start something but what happens is people … There is usually a person who’s in it way more than the other person. The other person is testing out several things and deciding which one is going to move. So you’re always going to feel …
Basically everything … I think everything is like dating. You’re ready to make a committed relation, you’re ready to have a committed relationship, you want to get married and she’s like, “You know, this might be good but I want to date five or six other people. Let’s see like whether there is attraction and let’s see where there is movement,” and I think that can be really hard when you’re committing and you’re there and you’re just like, “Well, if she’s not available, If I want to do this things that’s he’s not producing them.”
The gentleman that I was chatting about from MIT for example, he gets hit up all the time from people who want to do projects because he can code like crazy.
So think about trust, and it can be messy and I guess I want to dig in a bit for us because what’s the difference between looking for a co-founder and just hiring somebody to help you?
I think the difference is always around relationship. The thing that I was mentioning with Idealist, the notion that someone is really committed in the same way, it could just feel different. It could feel like, you’re paying me a salary of X and by the way, the other challenge of course is very often start-up mode whether there is a salary to draw from even. It’s always one big issue versus equity or other things.
But I’d say that I think that’s a big part of it is the notion of how invested that person is in that work. I think it could just be really difficult. One of the reasons I ended up doing so much senior advisor stuff is I need a lot of people who are starting things and I can go emotionally from zero to sixty on people’s projects. I love ideas, I love concepts so if someone starting something that they’re really interested in and I naturally gravitate towards, “Okay, let’s think about that,” and I’m interested in both the programmatic thing but also the emotional well being of the founder because very often founders are pretty emotional sort of fragile states because they have to always offer up this image of “I’m on top of it. I know everything. I’m smiling,” and I think that weighs on them quite a bit. That notion of having to be just to know everything.
I was at a fellowship retreat not so long ago with a group of founders of stuff and we had our cohort met and two thirds of the group of ten were just crying over this issue of like how difficult life was and how hard it is to try to always have to have this sort of mental of perfection, of being bright and shining and on top of things and impressing funders and donors and staff.
Yeah. It can be challenging to keep the game face on but I think you’re making an important point not only for people who are thinking about founding their own organizations or practices but just people in the workforce in general. We don’t all have to be perfect.
For the benefit of our listeners, you’re first start-up was idealist.org and I know that many of our listeners are big fans of that website where it provides positions for people interested in non-profit work around the world. Then you were involved in another organization called “All you possibilities” and that didn’t go so well. We’ve all had our failures and I certainly have and now you’re involved in a new group.
Just quickly Russ, can you take us through those three organizations in just a few minutes. Let’s start talk about Idealist. How did you know that was going to take off?
I didn’t know it would take off. We never do …
But in some point, you open the doors and then you’ve worked hard and then it wasn’t a start-up anymore. It was a successful organization.
After four or five years, we finally had gotten to a place of being desperate for money and we started charging people to post jobs. We had no choice and that took off. But for a very long time, every single time we would see a new big non-profit sector website appear. We would be like, “Oh my God. That one looks way better than ours. That one is going to just kill us. We’re never going to be able to last.”
I’d say it took us a very long time to feel really comfortable with that. We got to a point … you get to a point where you start to feel a little bit more [inaudible 00:29:11] in terms of how people are very aware of you in certain places. You start hiring people of course, but you feel anxious much of the time and even now and every single one of the things that I participate on this side, you never take for granted that thing is going to take off. You just don’t know. You see too many things come and go to be sure of that. So I think that’s one of the challenges. I think with all your possibilities, part of it was I just kept waiting for a sign. I got to a place with Becker and [Green 00:29:47] where I was a finalist. It didn’t happen. I was like, “Well, I guess that’s my sign.”
But it was more just like this emotional difficulty of moving ahead.
I want to talk a little bit about that because we … I think we all whether we’re starting an organization or we’re involved in a project at some point we have to make a decision to let go. Tell me when you decided … First of all what was all your possibilities and very quickly and when did you reach a point where you thought it wasn’t just going to go forward?
The idea was that it was an opportunity to go and offer mentorship and locational opportunities advice for LGBTQ young people. I really like the idea of that and connecting people geographically and letting people find based on certain ways that this helps identify whether location or faith or background et cetera.
I’ve done a lot of work thinking about it. It was a very good idea and I just wasn’t at that moment equipped to deliver on. It’s one of those things that remains in my head as a thing that I come back to. Conceptually, I tend to have these flashes of ideas of things that I have to do and will sort them out and share them.
I got to a place where I was just like, “Why am I having difficulty moving this thing ahead?” Actually as that was happening, and I was struggling, Elliot who is at Clearly Next, he and I …
So he is one of your fellow co-founders at Clearly Next.
He is one of the founders for Clearly Next. That was three of us, Bill as well. We’ve been introduced about the year and a half prior to a second conversation. The first conversation, it was 20 minutes of him talking at me and then 20 minutes of my talking to him. “Okay. It was great chatting,” and it will follow.
Just like we both had a piece and then we were done. Then a year and a half later, a funder said, “You two should talk,” and then a year and a half later another someone from a [inaudible 00:31:48] one of those places said, “You guys really should talk,” so we spoke again and we were just at different places emotionally. We realized that we were just … we needed to have another person that we could work with to move ahead.
And this is how you got Clearly Next off the ground.
Yeah, that’s how we started really working and he also had previously been a founder and was a recipient of the Ashuka. He had also been accomplished. The other thing that happens … I mean this is not a conversation about what happens or you could be a one hit wonder, that’s a whole other thing.
But I think there is this notion of you’ve start an organization. Do you have another thing … Is it an idea that matters enough, is it a thing that you care about enough that you want to go out and you have the energy to do it again.
So when I was at Idealist, I was in my 20s and I had just ridiculous energy for stuff and it wasn’t … There is a thing about social capital. You’re less nervous earlier on like “Am I going to look bad or am I going to embarrass myself in front of people,” and actually move along further along your career, you have more in clarity about that. So you’re more aware than, I think that was another part of the endless possibilities. I was like, “Either I personally do this.”
When I talk to people about founding a thing, I always will sort of say, “Here are the three questions,” which will be what’s the void you’re trying to fill, how are you going to sustain this long-term and then I’d say, “Everyone is going to ask who the hell you are to do this.” If you can give me those three things, that will take us a long way towards seeing if this makes sense. What’s the void, how do you know it’s a void, what’s the research you’ve done, how you’re going to make sure this is going to continue going long-term, is there a market whether a non-profit or consulting or for profit, how do you know there is a market, how do you reach to that market and then when people look at it at some level, they are going to say, “Why should I listen to you versus the other people?” I think you should always have to come up with the responses to that and that’s challenging.
Those are great questions though and I think that’s a great point to close the interview.
Thanks for joining us Russ. You can find Russ online in two websites; Clearly Next and Talent Philanthropy. Those URLs are clearlynext.com and talentphilanthropy.org. We’ll be sure to include both sites in the show notes. Thanks Russ for being here.
Awesome. Thanks for having me.
All right. Take care.
We’re back in the studio. Cecilia, Ben what you two think? What are the two take always you got from that conversation with Russ?
The main point it brought home for me is that some people are just suited for this type of path and one way to figure that out that Russ talked about was being okay with not knowing where it’s going to go and being okay to take that risk, work really hard and see if it pays off or not because some people just can’t be in that type of mind sets so I got a lot from the interview that was probably the main thing for me.
So don’t be afraid to take the risk and go down the road but also recognize that you may find as you do that that it’s not the right path for you.
I really liked his point about having a support system around you, whether that is a mentor or a advisor or maybe a board member if you’re starting a non-profit. Having a group of trusted people that you can bounce ideas off of and that you can listen to and who can’t ignore. I think it’s so important because having a support system around you, people who can listen to you, validate your ideas or sometimes play the devil’s advocate and say, “That’s not a good idea. That is so important to success.
I agree. I think that’s excellent advice. Whether you’re thinking about starting your own gig or thinking about you’re next job..
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