Ted Rheingold wondering how IT IS he became “The Dog Guy”

What I Learned Building A Startup like Dogster, Inc.

This just won’t work in paragraph form as nothing in a startup happens in a linear manner. It’s all happening at once, always and the realization of any learnings come to you in no particular time frame after that.

In startup land, if you build a sustainable profitable business that is not growing greater than 50% a year, everyone will respect you individually, but few will respect the actual profitable, sustainable business. Seek their respect at your own risk.

If doing what you love (in my case making Internet products that help people connect) allows you to make a business out of it, you’ll end up hating what you created because all you get to do is manage a very complex, challenging business.

Once I created a successful service and business out of nothing I became a lot more scared of blowing it than anything else, when really I should have just been content that I had succeeded at each previous step. It’s important to yell out loud “I did it!” to no one in particular when you realize you achieved what was once a goal. (See Louis Season 3 Episodes 10-12)

If you do not prioritize friends, family, loved ones, pets, plants, hobbies while working on a start-up they will decay and extinguish. All you will be left with is a startup.

The modern press will believe almost anything you tell them. See my lower point about selling 50% of the time.

If you have enough courage to run your own business, it is roughly 1,000,000 time more rewarding than any job available, assuming you can make enough money and value out of it.

If you hire friends you will have to work 2x as hard at maintaining your relationship as before, or you’ll likely be neither friends nor coworkers for long.

Don’t believe anything you whiteboard. Ever. Only believe what you see customers enjoying.

Treat your employees as you wanted to be treated at your first jobs. Fight, fight, fight any urge to do anything that would sound condescending, belittling, demeaning, etc. They are people seeking happiness and security too. Yes it’s infuriating that an employee might not understand the profound gravity of an issue that has consumed your entire being, but I bet if you stop you’ll realize you haven’t trusted them too. While I rarely found this helped make good opportunities great, it made awful events manageable.

If and when you are rude, disrespectful or go over the line with a team member, no matter the reason, apologize right away. Explain why it happened, why it was wrong, and be sincere about it.

When you’re out at an event and someone asks how you are doing, avoid the temptation to tell the truth, as you might horrify them. Save the specifics for friends of the business. A great catch-all response to the always-asked “how are things going” is to give a double thumbs up and say “Great! You?” If you do have good news to share, keep it to the single best item, and say it with some humility. If things actually are great, avoid the deep yearn to go on and on about it. At best it’s boorish, at worst it creates animosity. Save it for the insiders.

Hire slow, fire fast.

Fuck up fast.

Founders need to be selling 50% of the time. This sounds obscene to a product maker, but making great product rarely ever ensures your business’ success. Founders have to be selling to investors, customers, employees, press, industry. Any founder that isn’t shouldn’t be a founder.

Make time for team fun even when budgets or available time doesn’t allow. Buy everyone ice cream. Go to the beach. Have a hand stand contest. Watch youtube videos together.

When communicating with investors do not share good news until it’s a done deal. Nothing worse than having to answer you got left at the alter when an investor asks how the big new partnership is going. (But also see @Sacca’s note to the right. Don’t withhold bad news, be the person your investors hear it from first.)

Business partnership contracts are not to lock in your upside. They are to defend against downsides. You are responsible for creating and ensuring your own upside, no matter how the contract is worded or what you think you’ve gotten them to agree to.

If you are succeeding you will have competition, usually from the biggest players in the industry and most clever starters from the bottom. There is no exception to this rule. When starting up, one year’s success will never be the next year’s success.

Don’t let success entice you to move your goal posts of personal success. Always take the time to recognize when you and your team members hit their original goals.

Build goodwill whenever possible. If you’re not getting a lift up by someone, you should be giving someone else a hand up.

Be polite. A public thank you by twitter is almost as good as a hand written notecard if you do it sincerely.

Be careful about letting your mouth run at those open bar events ;)

Industry distractions can be brutal. If you’re having a hard time focusing on your own destiny, tune out channels like twitter and start-up blogs. While you may read 10 things a day that you think might be able to help your business, if something actually will, 3 different people will email it to your inbox.

Every other founder is lying awake at night ruminating over intractable problems and insurmountable requirements. Talk to any of them one-on-one for more than 5 minutes and you’ll be in a spontaneous therapy session. Have these therapy sessions as often as possible, as going it alone is exhausting. As Ben of Andreessen Horowitz said:

As a startup CEO, I slept like a baby. I woke up every two hours & cried.

Recessions and economic downturns are easier periods to compete than periods of strong economic fundamentals.

Finally, stick to your motherfucking guns!


Find Ted Rheingold on twitter for more stories to make you laugh and cry.

You can find our about Dogster & Catster on TechCrunch, as well as here, here, here.



Wrestling with stage 4 carcinoma thanks to amazing researchers and oncologists. Passion for making the Internet do exciting and wonderful things.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Ted Rheingold

Wrestling with stage 4 carcinoma thanks to amazing researchers and oncologists. Passion for making the Internet do exciting and wonderful things.