Starting Up Again, One Year In

Somethings old, somethings new, and lots of fun with friends

If you’ve ever started a business you’ve had thoughts of looking forward to the day when you can start over again, applying all of the lessons you learned in the current one. One year ago I jumped into my third startup and fourth entrepreneurial venture with Hearty. It feels appropriate to reflect on the journey so far and how it feels different—and better—this time around.

I admit that jumping straight from a successful startup exit into a new venture keeps you humble and on-your-toes. There’s little time to bask in past victories with a new season at hand and the scoreboard is blank again. I’m thankful for the chance to keep playing—especially as part of an amazing team.

Sometimes I feel like a veteran athlete in this league of tech startups. The game is constantly changing and evolving, and there’s always a new crop of young talent rising up to challenge you. I don’t have as much natural energy as I used to, and my game is a bit “old school.” But like a crafty veteran I’m now more efficient with my time and talent, willing to adopt moves of the youngsters, and get to apply what I’ve learned over decades in game. Here’s how I’m tweaking my playbook this go-around…

Fixing Past Errors

It’s funny, when people ask about the history our last successful startup, Ahalogy, I tend to first reflect on all of the mistakes we made along the way. Going further back, when people ask me about my time working on in new products at P&G. I tend to first talk about my role in the massive failed launch of Fit Fruit & Vegetable Wash, rather than our later success with Mr. Clean Magic Eraser. I think I keep the failures and mistakes top-of-mind so that I (and others) don’t repeat them. And I love having the chance to avoid them now.

The biggest difference with Hearty so far is that we started with months of customer interviews. This is something the textbooks tell you to do, but it’s so hard when you have an idea in your head and badly want to start building. This time we truly started from zero and let the conversations with future customers and industry experts guide our thinking and decisions. We dug deep with a range of people from large and small companies, and we debriefed each discussion carefully. Now we have these customers in our heads and copious notes to go back to.

Second, I looked back and realized that I didn’t spend enough time on the product side of Ahalogy early on. Back then, my co-founder took that side of the business and I trusted him to handle the vast majority of the tech decisions and team. I think I was too intimidated to lean in since I was not a developer myself. A few years later when he left and I became CEO, I had to work hard to get a handle on the product and the team. That led to several issues and a complete turnover of the team. Thankfully, our third CTO, Ross, was the charm, and I got closer to the product without getting in his way.

Flash forward to Hearty and I feel more like part of the product team, helping guide strategy, QA-testing, and writing copy. I’m not coding, and my eyes glaze over from time-to-time in discussions, but I know what’s happening and am learning more than I ever have about key technology decisions.

Some of my biggest past stresses and screwups came around outside investors. We made every mistake in that book: Raised too much, spent too quickly, had too many investors, and looked at fund-raising as the goal—rather than actually building the business. Thankfully we corrected a bunch of mistakes mid-stream, got profitable, and everyone did really well in our exit.

This time we’re starting with a much more fiscally conservative approach. Raising money should come in two waves: (1) a small amount to experiment and find product-market fit; and (2) fuel to scale up—if and when you really need it.

So we began by investing our own money this time. We’re keeping the team small and budget tiny. We’ve raised some money (news to come), but kept it with a group we already know and trust. Ironically, this type of approach gives a startup much more freedom, as you’re not immediately tied to a specific idea, investment path, or growth expectations.

Repeating What Worked

Avoiding mistakes is great, but we’re motivated to double down on the things that worked before. You have to be careful not to just blindly repeat what worked last time, but there are some general success factors that we are re-committing to.

The first and biggest is working with people we already know and trust. Our small group has been through years of building together. We know each others’ strengths and weaknesses, and we accept and work with them. We aligned on what motivates us and where we want to go from here. This allowed us to skip the Forming, Storming and Norming steps (and risks), and go straight to Performing. The efficiency and enjoyment that comes from getting the band back together like this is remarkable.

Second, we’re working on a product that addresses pain points we have felt and know well. At Ahalogy, I was building a marketing product based in part on my experience as a brand manager. I could always channel that perspective into our own product, sales and marketing choices.

Hearty is about great people helping each other find opportunities and make hires. We’ve used our networks extensively in our careers and seen the many challenges in activating them efficiently. We’re heavy, paying, frustrated customers of the only current technology solution in this space, LinkedIn. This makes our decisions faster and stronger.

Aside from experience, this is another company where I get to follow my calling to make a positive impact on the world. As a marketer, I developed a belief in Marketing with Meaning—advertising that adds value to consumers’ lives. I co-founded Ahalogy in large part because I saw an opportunity to build a company that created marketing with meaning in the form of useful content from passionate creators.

As my career has proceeded I have increasingly shifted my passion toward team building. After growing a couple of businesses, I have come to see that people are really the key to success—and what makes all the work worthwhile. For me, Hearty represents an opportunity to make a big positive dent in the world by helping build many more amazing teams of people.

The Journey > The Destination

We’ve barely started Hearty, and I don’t have any regrets or mistakes of note yet. It feels like we’re moving quickly and our product is progressing faster than I expected. We’re already making job matches among our early members, and just yesterday saw about 15% of our entire membership on our app in a single day without any major news or nudging.

Lots of founders on Twitter complain about how hard startups are. And it seems many who have had successful runs and big exits never come back. More than one friend suggested I take a at least a year off before getting into the startup game again.

Well, it’s certainly not an easy job; but for me, entrepreneurship is the best fit between my skills and passions. It’s like a big game with tons of imbedded puzzles and side quests—a real life Dungeons & Dragons. If you can’t look at startup work in this way, then it’s probably not for you. I readily admit—and my wife reminds me—that I’m a weirdly wired person.

I am much more relaxed this startup season than the last one. I’m enjoying the ride more, and have a lot less fear of failure. They say the opposite of fear is not courage, but love. Lots of things get clearer and easier when you love the work you do and the people you work with.