Entrepreneurship With a Family is for Crazy People

I am frequently asked how I was able to go out on my own with a family of a wife and 6 kids. The truth is I’m crazy – completely crazy. If you want to see how crazy entrepreneurship actually is go follow my friend Dave McClure and listen to a few of his presentations (warning – lots of language). Entrepreneurship, without a family, isn’t for the faint of heart. This is my story.

Entrepreneurship alone is tough – really tough. Your chances of going completely broke are 9 out of 10. People call that failing, but the truth is most entrepreneurs don’t just fail – they lose all their money, and their credit cards in the process. It’s tough – it’s really tough.

I used to think that every entrepreneur out there had a lot of money – they were able to go out on their own after all and support themselves. How do they do that? The truth is most of them are just like that commercial of the neighbor with the nice house, nice lawn, and everything you ever wanted, culminating with the neighbor saying, “I’m in debt up to my eyeballs!” That’s the truth for most entrepreneurs. Without a family, that’s a risk many can take.

Add to that a family – a family of 6 kids nonetheless – and you can see how crazy it actually is. Not only am I risking my own finances. I’m risking my ability to keep a roof over my family’s head, the ability to keep food on the table, pay for braces for my teenagers, and give them a good life. Babies become more expensive (if you want more). Health problems are more expensive. It’s not easy at all.

If you’ve gotten this far after being scared out of your mind you’re ready for entrepreneurship with a family. There are rewards as well. On top of it all, you get the freedom to set your own schedule. You get the freedom to be with your family whenever you want. The last time I was out on my own I spent an entire month on a road trip with my family going to Boston to see my family. I managed clients all while on the road. A day job would not have allowed that.

So if you’re still interested in starting your own business and going out on your own with a family, here are some tips, and a few warnings. I’m not perfect at it yet. In fact there are times I’m still desperate and trying to find the one thing that “sticks”. However, this is what I do and remember again – I’m crazy. I’m going to address this to the men and husbands of a wife, because that’s the only perspective I’m familiar with – I’d love to see the perspective of a wife some time though. Here are some tips to get you going:

  • Health insurance – there will be expensive options that come about as a result of Obamacare (whether you like it or not). I find that those work well if you have a pre-existing condition. You’re even crazier to be an entrepreneur with a family if you have a pre-existing condition.

    What I do is I get a healthcare plan with a $5k-10k deductible. There are many companies and options out there that offer this – Google it. This usually covers catastrophic issues like cancer and surgery and other things like that, but for anything else, better start saving your money. You can also negotiate better with Doctors if you don’t have insurance because it reduces their cost of having to deal with and wait for insurance companies to pay them. Remember – they’re crazy entrepreneurs too!

    Whatever you do DON’T GO WITHOUT INSURANCE – that’s not only crazy – it’s stupid. Get something with a high deductible and everyone will be happy.

  • Focus – This is a huge problem for me. I have so many things I like to try out and play with and hopefully make money out of. Figuring out which one to focus on is always the hardest part. Focus on the things that make you the most money NOW. Don’t do things that don’t have monetary value. If there’s a royalty vs. an advance I always take the advance because you can never guarantee the royalty. Only add other things to your workflow after the things that are making money are actually supporting you. Some times this involves working a full time job as that main means of revenue.

    I like to close down Facebook and email and put my phone in another room when I need to focus. That’s really tough to do, but it does wonders at making you focus on what you need (even writing this post is a distraction for me, but I feel I need to document it).

  • Investment – take it if you can. I tried to bootstrap my first business. I had no idea what I was doing. As a developer and marketer, I can build things and build audiences, but building those things into a true business that is sustainable is not my strong suite. Seeking investment up front from someone that could help with the business side of things would have been a huge advantage. I’ll add to that partnering with someone with such expertise would have really helped.
  • Dealing with the family – your wife is going to hate you for putting your family through this. I don’t know an entrepreneur with a wife and kids who has not had a few arguments with their spouse on why they should still be doing this. Be prepared for that.

    It’s important that you give your wife and children the time they need – maybe spend a day a week to just them. Another option is to make sure you’re having family dinners every night and that you’re a major part of that. Or perhaps you have a family night once a week. Go camping with them once a month – I find that really builds the family and gets you away from technology and the distractions as you do it.

    You’re also going to need to fulfill your duties as a husband and father – that means supporting the family. ALWAYS HAVE A BACKUP PLAN. If you run out of money don’t put your family into debt. Give yourself enough runway that you can get a job if you have to. DON’T BE AFRAID TO GET A JOB! You’ve got to find ways to put food on the table and make your house payment/rent.

    My Uncle, who founded Freeservers.com, Unitus, and several other successful ventures, always tells me to have a date you and your wife set where if you’re not profitable by that point you will get a job. Do that and stick to it and your entire family will be happy.

    Your wife is going to need to trust you – build her trust and she will. That means she has to feel secure and safe in what you are providing for the family. Include your wife in the business, and make her a partner as much as she is willing. Don’t do it if she’s not in it with you – that’s stupid too.

Being an entrepreneur with a family is nuts. You are nuts for trying it. However, if this is what you do like I do and this is what keeps you going, go for it. Go all out. Change the world. Make things that the world has never seen before.
Entrepreneurship is the happiest I’ve ever been. It’s the best job I’ve ever had. It’s the most successful I’ve ever been. But it’s also been the scariest time of my life and a place where I’ve also seen the greatest failures.
I hope these tips have helped at least some of you – if anything it should be a voice of warning before you try anything. I don’t mean to scare anyone away from entrepreneurship. I do mean for you to be completely aware of what you’re getting yourself into before you start. These are waters that you will drown in if you’re not careful. Tread carefully, and you’ll have one of the most rewarding experiences of your life. Swim on my crazy friends!

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Jesse Stay has been a pioneer in the space of social media marketing since before it was called "social media marketing". Originally a software developer, Jesse built a tool called SocialToo.com which helped brands like Pepsi, Brittany Spears, and MC Hammer grow their social media presence, and before he knew it brands were coming to him for help to grow their presence in very unique ways. His tool was featured on almost every tech blog and even mainstream news sites like New York Times, Techcrunch, and Mashable. Jesse also spent a brief period working FOR Facebook, Inc., helping them to build out their documentation to help companies integrate Facebook Connect into their websites and mobile apps. Jesse took his skills and helped the LDS Church kick off most of its social media programs. While there he helped launch the award-winning "I'm a Mormon" marketing campaign with global reach worldwide in the millions of views and followers. Jesse established new global programs at the Church to further grow its reach amongst both members and non-members of the Church, working with every department of the Church, also including entities like the Mormon Tabernacle Choir and Brigham Young University. He also helped the Church navigate its voice and presence during the Mitt Romney Presidential campaign due to the significant attention the Church was getting at the time. He established the social media advertising techniques and strategies employed at Deseret Digital Media growing over 20 million fans across their news properties in just 6 months, and was featured on AdWeek for his success. As founder and Principal of Stay N Alive, Jesse has developed very unique techniques in social media advertising to help organizations grow presences, within months on minimal budgets, into hundreds of thousands of highly relevant and engaging fans and followers. He designed and teaches social media advertising at LDS Business College. He has helped grow sales, and has a belief that yes, you CAN measure social! Jesse has been featured as one of 10 entrepreneurs to follow on Twitter (next to Biz Stone and Ev Williams, founders of Twitter) by Entrepreneur magazine. Jesse has written 9 books on the topic of social media marketing and development, including Google+ Marketing For Dummies and Facebook All In One For Dummies, and eats, lives, and drinks social media with a personal combined presence of over 600,000 followers on his personal social profiles.

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