Gena Shingle Jaffe of Genavieve Shingle Jaffe is a lawyer turned online entrepreneur who helps other entrepreneurs deal with the legal side of their businesses. Gena's story starts out working at a law firm in New York City then taking the leap to self-employed after meeting other entrepreneurs and seeing the impact they were having on other people and the freedom they had themselves.

Her journey to where she is now wasn't always easy (she tells us about the time she had to start over with less than a quarter in the bank!), but she proves that even with no prior experience a plan, hard work, and a solid network cheering you on can make all the difference in your business.

Here's what she has to say...

You work outside of the 9-5, but you went to law school. How did you make that decision to leave?

I never had any intention of leaving the corporate world. I never was really exposed to entrepreneurship. My parents are working class so for me it was like - you go, you get your degree, you work until you can retire, and live off of your 401k which sounds pretty boring but it’s what I knew.

There’s security and stability and I really valued that. When I met my now wife, she was a business coach at the time.

She was like, “You should start your own business” because I was unhappy and I was working all of the time and I was just burnt out. I was a corporate lawyer in New York City.

So about six months into us dating, I was like, “You know what? I’m just going to do it.”

I saw this huge market opportunity where there were so many entrepreneurs and not many lawyers that serve them. I made the leap in January 2014.

It’s been crazy. It’s been great. It’s been scary. It’s been a rollercoaster. But, I’m sitting in my own house right now, so I’m doing pretty well.

Gena Shingle Jaffe of Genavieve Shingle Jaffe is a lawyer turned online entrepreneur who helps other entrepreneurs deal with the legal side of their businesses. In this week's Make Change, Gena shares how her journey to where she is now wasn't always easy (she tells us about the time she had to start over with less than a quarter in the bank!), but she proves that even with no prior experience a plan, hard work, and a solid network cheering you on can make all the difference in your business. Click to read on.How did you make that shift going from corporate lawyer? Did you start as a side hustle or did you quit and start your business?

Because I was working in a law firm, I couldn’t have a side business doing legal stuff. So what I was doing is connecting with people. With my wife being in the industry I met a ton of people who were like, “We need you.”

So I walked in having clients right off the bat which is amazing.

I hired a web designer to get my website up and running and I was polling, seeing what people might need. I was asking friends who were entrepreneurs, you know, “Where do you see the gaps?” and then coming up with different offerings so I was ready. And the day after I quit my job my website went live.

What were those first steps when you started working? Where did you initially put your effort?

I didn’t know anything other than working with clients one on one so I offered a ton of free calls with people to really talk with them and see where they were and let them know what I thought they needed.

I was working a lot and I was like, “wait a second…”  It was great that I was working a lot from home, but I also wanted to have more flexibility in my life so about three months in I decided to offer more passive products.

I started selling Google Templates and I created a legal course. My wife was working with private clients, but she also had a group coaching program and I wanted a group program, too but I don’t know how that would work as a lawyer.

I hired a coach and we figured out how we could package things together so I could work with a lot of people at once and give them the things that they really needed. That sort of turned into my bread and butter.

I read on your blog that you went through B-School with Marie Forleo. Tell me about that experience?

I actually bought B-School a month into starting my business because my coach had taken B-School in the first generation. It’s such an incredible place where you can connect with so many people - the Facebook group is full of thousands of other entrepreneurs.

Coming from working at a law firm I had a good amount of savings put aside already so the two thousand dollar investment wasn’t a ton for me and it was going to make me money because I connected with people and got a ton of great content.

It was well worth the investment - I’ve gotten a lot of clients and business connections. And Marie is my hero.

You had a website, contracts, then courses. How did you go about choosing to create courses over other alternatives?

Back in 2014, membership sites weren’t as big as they were now and podcasts weren’t as popular either. Only bigger people had podcasts.

I feel like a course is less than an investment timing wise. Podcasts you have to do every week or every month but with a course you can reach a lot of people at once but it’s pretty passive the way I have it set up.

It seemed like a no-brainer because I saw so many people do it. I hadn’t found any other lawyer doing a course so it took a little bit of brainstorming and trial and error to figure out what to do because it hadn’t really been done before.

So I did a beta run where it was inexpensive and I got a good amount of people to sign up for it. It went really well and those people became my testimonials and they told me what worked and what didn’t.

From that beta, I turned it into a full course that did have that backend membership site.

It was good for me to see what worked, what didn’t, and what I liked and what I didn’t.

Gena Shingle Jaffe of Genavieve Shingle Jaffe is a lawyer turned online entrepreneur who helps other entrepreneurs deal with the legal side of their businesses

Can you dig into a little bit about how you refined your idea for this course?

I did a four week course where they got four legal templates and each week was a theme like “client contracts” or “privacy policies,” stuff like that.

I had office hours in the Facebook group where people could ask questions, and I did a Q&A call.

From there I saw what people liked and what people didn’t respond to, and I could see what format I liked so I threw in more contracts and made it so it was self-paced. So once you signed up you got everything and it was up to you to watch the lessons on your own.

I still did Q&A calls and I still had the Facebook group where my students could ask me questions.

You talk a bit about your first business failure on your blog - can you tell people what you went through?

First - I don’t like calling it a failure. I like looking at more as a lesson.

My first nine months of business I made six figures, but after my first year of business, I almost had to file bankruptcy.

What happened is I invested in everything. I bought so many courses and hired so many coaches and I traveled the world going to conferences and events and retreats. I learned incredible things, but I didn’t take the time to implement them because I was always going to the next event or the next retreat. I took 30 plane rides that year - it was too much.

Coming from corporate you’re used to that steady paycheck, and one forgets that not only do you have business expenses, but you have your life expenses. I was living in New York City and I didn’t really change my lifestyle.

I also got married that year. There was just a lot that was going on. A lot of stuff, a lot of expenses, and I had 23 cents in my bank account at one point. 

I went into a really deep depression because it felt like everyone warned me when I started my business that I shouldn’t and it felt like it was coming true. Everyone’s fear - my worst fear - it’s was happening.

It was really hard and I felt a lot of shame and embarrassment around it. Now I’ve learned that there’s nothing to be ashamed of, but then I was going to go back to a law firm, I started to applying to jobs.

But then I decided that I’d give myself one more chance.

I promoted B-School that year and made a good amount of affiliate money and I decided that I’d give it one more launch.

I put everything into that launch - blood, sweat, tears, everything.

I made 170,000 dollars in that one launch and it saved my business - and my sanity.

I took half the money I made in B-School and put it towards that. I did Facebook ads, I hired a videographer, I had a launch strategist - I did a bunch of things that weren’t frivolous. They were so necessary in order to make this the big launch.

I got affiliates, too. I had other people promoting my course for me as well, and it ended up just being perfect. I’m so grateful.

Gena Shingle Jaffe of Genavieve Shingle Jaffe is a lawyer turned online entrepreneur who helps other entrepreneurs deal with the legal side of their businessesWhat do you think made your launch so successful?

Affiliates helped a lot. I got in front of so many people that I normally wouldn’t have gotten in front of. I give huge credit to my partners.

But also, a lot of it was my attitude and my mindset.

I was like, “This is going to work. It’s amazing, my course is amazing.” I did webinars, videos, I was in front of people all the time.

I was trying not to make it super salesy, but rather, inviting, like: this is what you need.

A lot of people told me that I changed the way that the law appears - it’s not as scary, it’s not as fun, it’s a little glittery and sparkly.

A lot of things went into it.

With your affiliates, what was your affiliate deal?

My course has changed since then, but back then my affiliates got 50% so it was the same system as the B-School set up. You got 50% when someone signed up with your unique link.

What is the biggest mistake you see entrepreneurs make in terms of how they’re applying the law to their business?

They’re not.

That’s it, they’re not. Or they’re just kind of whipping documents together. It’s better than nothing, but a lot of people will say to me, “I need to get clients before I invest in a lawyer.” But that’s a huge mistake.

Everything - your business, your brand - is on the line when a client hires you. I don’t like to use fear-based marketing, but it’s true.

You’re creating this business that’s like your baby and you want to protect it and that’s what the law is there to do. To protect you.

People don’t have legal as a priority when it should be.

What are the first 3 things that someone might need?

It really depends on the type of business you might have - as a disclaimer, this isn’t legal advice, just information because I don’t know your business - but if you’ve got an online service based business you need a client contract.

Something in writing that says: This is what I’m giving you, this is what you’re paying me, this is what you can do with the information I’m giving you, this is what you can’t do.

It’s really there to protect all parts of your business, and it actually protects the client as well to make sure that you deliver on what you promise. So it’s actually a really beautiful document.

And if you have a website you should have 3 documents that will protect you and your website:

  1. There is a disclaimer: This will protect your liability, meaning if there is something on your website that they apply to their own life and it doesn’t work out they can’t sue you.
  2. Terms and conditions: This protects the content in your website - the content and the copy - so people can’t just swipe your content.
  3. A privacy policy: This is legally responded in many states. This says that you might sign up for my email or buy something with your credit card and I promise that I won’t sell this information or spam you.

Those are the three very important documents.

High level: You’re now at a space where you’re running a successful business, what has been the best part of running your business?

Just having the freedom and flexibility to live my life while running a business. I’m pregnant right now, so being able to take time and be present and take care of my body - I was very sick my first trimester - that’s been such a huge gift being able to relax and rest when I needed it.

And getting to see family - I see my family and in-laws a lot. They don’t all live around here so being able to travel and see them around has been exciting.

What are your business plans for the future? Anything we should know about? 

I’m relaunching my course with a partner. The course is called Damsel goes bare, we call it a legal course with sparkle and soul. She’s very soulful, I’m very sparkly.

We’re launching that again in October, so super exciting. Then I’m taking time off for maternity leave.

Last question: What advice do you have for anyone out there who wants to take the leap and become an entrepreneur?

Don’t try and do it on your own. It can be very lonely being an entrepreneur - find a networking group, hire a coach, find someone to be an accountability buddy. You can do it, it just takes a lot of commitment, passion, energy, and time but it’s so worth it.


Check out more content like this

Back to Blog
Morgan Timm

Written by Morgan Timm

Morgan Timm is a content marketer at Teachable with a background in blogging and social media. She runs Mostly Morgan, a life and style blog that reaches an audience of 40,000 people monthly.