My Biggest Professional Mistakes

My Biggest Professional Mistakes

Recently I saw Jason Lemkin tweet his answer to “What Has Been Your Biggest Career Mistake?“, and it got me thinking about my own. I’m not quite a decade into my own professional experience, but after seven jobs and numerous positions, promotions, and a layoff I’ve made my share of mistakes. And what’s more fun […]

On Being Willing To Fail

On Being Willing To Fail

Too many of us live our lives in fear of failing. While some have a fear of flying, I think that once you’ve been through some great successes you no longer fear doing too well. The goal becomes to also be okay with the opposite – failure.

Anyone who is driven and wants to succeed must come up against this. It’s easy to stay in the known and optimize towards a 3-4% better conversion rate, but what happens when you want to 10x your business in the next few months? You won’t get there by doing tiny changes that get you .25% better (unless you are building off a huge base already). You have to change your mindset. Read more about On Being Willing To Fail

CredoCamp – Lessons Learned Working Remotely

CredoCamp – Lessons Learned Working Remotely

There are many perks to running your own business, and mine specifically lets me work with amazing marketers and entrepreneurs who can run their businesses from anywhere in the world. I’ve read so many books about remote working and how to set up a business that allows this. Books like The Four Hour Workweek and Vagabonding have inspired me while websites like NomadList.com keep me constantly dreaming. Even Facebook marketers are targeting me about traveling the world and working. Read more about CredoCamp – Lessons Learned Working Remotely

Bootstrapped vs VC – Building Houses Before Skyscrapers

Bootstrapped vs VC – Building Houses Before Skyscrapers

I love architecture. Part of the reason why I worked in rentals/real estate for a while was so that I could look at photos of beautiful apartments and houses all day while pretending to do work. I’m kidding about the pretending to do work part (mostly).

Houses mystify and excite me. My wife and I are thinking about building a house in the next couple of years, yet we have absolutely no idea where to start. Do we find an architect first? Should we buy land now or later? What about plumbing and electricity – how do we know how to set that up if we’re not in a development? We know where we want to end up – with a beautiful mid-century modern home in a beautiful setting – but how do we get there?

Bootstrapping a business is the same way.

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Why I Create Side Projects I Never Finish

Why I Create Side Projects I Never Finish

The Internet is littered with side projects that never received the attention they could have and thus never took off like they might have. I love side hustle post-mortems and stories of serendipitous things that happen because of them. Others have written on this topic, so now it’s my turn.

I would bet that every entrepreneur’s journey is full of these, and mine is no different. I’ve set out with big intentions to launch communities in a couple different areas I’m interested in (outdoors gear and cycling), bought a site to use as my home base as a nomadic marketing consultant (which never materialized), started writing an ebook about marketing that I never finished (but built a big email list for), and more. Each of these “failed projects” taught me something different that was valuable. In fact, I’ve come to think of each of mine as failed startups and now count them as part of my journey to finally having a business that could succeed.

Here are the lessons I learned. Read more about Why I Create Side Projects I Never Finish

How Getting Laid Off Led Me To Double My Salary and Follow My Entrepreneurial Dream

How Getting Laid Off Led Me To Double My Salary and Follow My Entrepreneurial Dream

Update: thanks for all the amazing reactions to this post! I have loved reading all of your emails/tweets/direct messages and hearing so many stories about people who have been laid off and it turned out to be a blessing in disguise. If you want to check out my company Credo, it’s right here.

I got laid off in September of this past year, somewhat unexpectedly. Things had been rough for a while as I moved to a new team internally after an acquisition and we tried to figure out how we supported my new role. Right after I moved over to the new team the GM in charge of that team left, which at the time felt like an omen and I came to realize later it was. When you lose the person who advocated to bring you to a new position, who has the vision for how that role will look, you’re going to be in for some hard challenges that you might not be able to win.

Today I want to talk about exactly the steps I have taken over the last few months that have led me to double my salary short term, which is how I am currently financing my software marketplace which is also growing substantially month over month. Read more about How Getting Laid Off Led Me To Double My Salary and Follow My Entrepreneurial Dream

Want To Be Successful? Become A Doer

Want To Be Successful? Become A Doer

I’ve been working on the Internet for what feels like a long time now – 6 years. In that time, I have worked inhouse for 4 different brands and consulted with more than I can reliably count. That number is probably in the 35-50ish range.

Over time, as I have gained more business experience and expanded my skillset outside of just SEO or even digital marketing, and am now running HireGun both as a consultant and a software solopreneur, I have increasingly become convinced of one thing:

Those who win are those who do

Many companies will say that they get things done. But the truth comes out when the rubber hits the road. When I worked at Distilled, we always prided ourselves on working with our clients to help them get things done. After all, if we were going to be successful as consultants, our clients had to see a return on their investment. If they moved slow, then it would take a long time for them to see that positive return and at that point it was up to the consultant to keep the client happy (and still a client!).

Here are some of the traits I have seen of successful companies and individuals. Read more about Want To Be Successful? Become A Doer

HireGun Launched Today

HireGun Launched Today

Today I launched HireGun (now known as Credo) to the world via Medium and Product Hunt. It has been quite the road to get to this point, most of which I wrote about over on Medium, so I recommend you go there to read the full story. I’m excited to have it out to the […]

Learning To Say No

Learning To Say No

Today I tweeted something that seemed to resonate with others. This was the tweet, with an embedded quote from this post (h/t Joel):

This was the quote:

“You can only go so fast for so long. You have natural output limitations. Other people rarely consider that when they ask for stuff and set deadlines. In fact, they rarely consider anything. Most times, I find the expectations that other people have around time are arbitrary. They don’t *really* need that thing right now–and if you gave it to them tomorrow, the world will go on.

Don’t be afraid to say, “It’s not going to happen by that time. Here’s when I can have it for you.”

There’s really no way to argue against that. If you draw lines and say no, they’re just going to have to figure out an alternative and accept. ” Read more about Learning To Say No

My Manager Hack: Relentless Transparency

My Manager Hack: Relentless Transparency

In my role at HotPads, I manage an ever-growing team of smart marketers. My job is to hire, train, and retain the best and smartest, with the goal of removing roadblocks that keep them from both working together and succeeding at their individual jobs.

I’ve had managerial positions before, but never this direct and I’ve never been able to build my own team. Building your own team is quite different from inheriting a team, which is a whole different topic I’ll explore at some other time. Read more about My Manager Hack: Relentless Transparency

I’m Not A Good Employee

I’m Not A Good Employee

Have you ever heard someone say “I’m just not an employee” or “After working for myself, I can’t imagine ever working for someone again”. I’ve often felt this way, even though I don’t work for myself (well, there were those two weeks).

When I started my job at HotPads back in October, I told my then-boss “I have to be honest with you – I’m not a good employee”. What I meant by this is that I hate to be managed by others. I want to explore this a bit more, because not everyone who hates to be managed can work for themselves. Sometimes, we must learn how to succeed as we are, where we are. Read more about I’m Not A Good Employee

Interview with Entrepreneur David Hassell, CEO of 15Five

Interview with Entrepreneur David Hassell, CEO of 15Five

Entrepreneurs are some of the most interesting people in the world. I recently had the pleasure of interviewing David Hassell, who is the CEO and Founder of 15Five, a product built to better enable managers and employees to give and receive quality feedback in less time. Throughout this conversation we talk about not only entrepreneurship, but also productivity, the power of why, and the driving force behind what he does. Have a listen/read!

Here is David’s official biography, and you can read their blog here (including an interview with Simon Sinek on The Power of Why):


David HassellDavid Hassell is a serial entrepreneur and CEO of 15Five, a software company focused on producing transparency and alignment in organizations through structured, efficient and effective communication practices. David has also been named The Most Connected Man You Don’t Know in Silicon Valley by Forbes.



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Talking Entrepreneurship and Product Marketing with Dan Martell

Talking Entrepreneurship and Product Marketing with Dan Martell

Entrepreneurship is a hot topic these days, and one that you may know I am quite passionate about if you are a return reader here.

After I interviewed Leo Widrich of BufferApp a couple of weeks ago, I was put in touch with Dan Martell who is a B2B SaaS founder coach as well as former founder of Clarity.fm, Flowtown, and Spheric Technologies.  Clarity exists to connect experts with other entrepreneurs in order to create a knowledge-sharing ecosystem where the experts can also earn some money in return for having conversations with those seeking to learn from them.

Fun fact: you can book a call with me through Clarity: https://clarity.fm/dohertyjf

We talked about products, the importance of focus, the importance of revenue generation as early as possible, freemium, entrepreneurial goal setting, and more. Have a read or listen and let me know your thought in the comments!

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