Why Being a Remote Startup CEO Doesn’t Work: My RipFog Story


I spent the last year trying to incubate a company in Portland from the Bay Area. It didn’t work out. It was not a unicorn (more of a gremlin). But it’s all good. Here’s the story.

Some of you may recall that, out of desperation, I set a timer for myself to start a company. My recent attempts at finding work had failed the passion test. The critical voices in my head were causing me to crack. My brain was like the stoning scene from Monty Python’s Life of Brian.

I wasn’t convinced doing another startup would be ideal, but it was movement. And staying busy is a good hack to keep the demons at bay.

Having grown a company in Portland back in “the naughts,” I knew a lot of really talented people up there. And they were all in the market for something more interesting to work on. My thought was that we could build a product in Portland, and find the people to sell it here in the Bay Area. Ergo, the name RipFog: Rip City (Portland) + Fog City (SF). For 98% people however this become RipFrog, even if they were staring directly at the written name. Apparently frogs are linguistically dominant.

So when one of my old architects from my previous company in Portland had an idea, we jumped on it. It was a brilliant, highly-technical idea, and way out of my sweet spot. But bumbling my way to knowledge was part of the fun. We raised some seed money, hired a small team and went at it – they in a cool office in Portland’s Pearl district, me staring longingly at said office through video conference on a rolling monitor, like a wistful Max Headroom.

I got to know the problem space, then polished up my wingtips to pitch it a hundred different ways to a hundred different potential users. I flew my cofounder down from Portland to the Bay for marathon days of feedback meetings.

Early signs were positive, partly due to it being a new domain. Plus we were talking to friendly folks who tell you what you want to hear. But as we got further into it, we realized it was going to be a tough road. Developers loved it, but they’re notoriously cheap. The people with money didn’t get it: the product wasn’t solving a deep business pain point yet, just a technical one. It’s possible to build a business around developer needs, but not the business I wanted to run.

After five months of building and pitching, we took stock and decided that it wasn’t going to work. Over the holidays in a hotel room in Ashland, OR, I even put together a plan to merge the company into another startup that was starting to get traction.

I thought the merger was a great plan, but the Portland didn’t share my enthusiasm. This was for a Bay Area company so a merger would make them the remote Max Headroom group.

But we still had some cash in the bank and a lot of ideas. So they were keen to take another swing at the plate. I went along with it.

That kicked off a process of ideation and product iteration. I would come up with ideas, meet with experts in the Bay Area to test those ideas, and then fly up to Portland to further refine the concepts with the team so they could prototype.

Ideation is normally a really fun process: whiteboarding big ideas and open space for how you can change the world. But doing that much of it by yourself and/or remotely sucks. You need the collaboration and whiteboard time. My team was amazing and I loved being up in Portland, but it wasn’t feasible to be there full time given my family and Bay Area-native wife.

After four months of grinding my brain, and meeting with anyone I could for idea feedback and frequent trips to the Rose City (maybe we should have been RoseFrog), we finally honed in on an interesting idea that had legs. And we built out an initial product with 20 different companies trying it out. Problem was: we were running low on money.

While I could have raised more money and kept it going, I didn’t want to run it remotely anymore. The team needed direct, collaborative leadership if it was going to succeed, especially in this “figure it out” stage. I was exhausting myself AND doing a bad job.

It’s one thing if the product ideas are coming out of Portland (like the original idea) and I can focus on selling it. But when it’s on my shoulders to bring new ideas for them to go build, it just didn’t work. If we could have been in the same office, it would have been different.

I thought of finding someone in Portland who could lead the team. We talked to a few CEO folks and even had a great candidate lined up. But the team didn’t want someone else. And the new product ideas were getting further away from the engineers’ passions.

So rather than raise more money and keep going down this uncertain road, we decided to find a good home for the company. Sad for me as I loved the team and felt like I let down them down. But it was the best decision.

My big takeaway: it’s okay to be remote if it’s a known category and everyone knows what to build and sell. But for a new idea, you need to be in the same room. That, and stay away from “Fog” in your name.

While not the ideal outcome, it wasn’t a bad one. And we had a good time, met a ton of amazing people, found a great company in Portland to acquire the team and IP. And we didn’t raise a lot of money so we were able to keep our investors chips on the table (i.e. they got equity in the acquiring company).

And those voices in my head? Much quieter now. More like the “Always Look on the Bright Side of Life” scene.

Most importantly, I learned a lot about myself and what makes me happy. The experience has been the catalyst for a few new passion projects. Stay tuned on that.


Craftwork: How Building a Dollhouse Made me a Better Boss

I’ve always been jealous of people with hobbies. I aspire to have one, but my overly-linear “does it move the ball forward?” filter for life has held me back from an all consuming passion for baseball cards, stamps or old daggers (seriously–Angelina Jolie collects them).

So I was out of my league when I went to a hobby store a few years back on the hunt for a doll house. My daughter was obsessed with doll houses and wanted a “real one” to be her big Christmas gift.

In a split second decision that would haunt me for the next year, I decided to go with the kit instead of the pre-built house as a “fun project to work on together.”

If you haven’t been through this before, a doll house “kit” is something only the guy from A Beautiful Mind could love: a giant box overflowing with thousands of tiny, unidentifiable, easily misplaced pieces of wood, all of which need to be organized, inventoried, sanded, painted (in a specific order), trimmed and varnished, all before you assemble anything.

Sundays over the next year became a mess of paint, glue, obsession, frustration, and trips to the hobby store, where the kind and crafty older women looked at me like a 5-year old who planned to build a car.

Continue reading at Inc.com.

6 Ways ‘Over 40′ Entrepreneurs Can Outpace Younger Rivals

I was 29 when I started my last company. This time I’m 42. Things are different.

Last time, my spare time got filled up with indie rock shows and small batch tequila tastings. This time, it’s more kid’s soccer, kid’s things besides soccer, and the occasional colonoscopy.

My workouts used to include tackle football and full-court hoops. Now I get injured doing pilates.

My big concern back then was a ponderous, “What do I do with my life?” This time, it’s a frantic, “Ack! I’m gonna die. What do I do with my life?”

Starting a company at this age has a lot of stark differences as well. First off, you’re no longer as interesting. At least here in Silicon Valley, where youth reigns. At this point, the VC’s seem to be honing in on 6th graders.

And there’s a reason for that focus on youth: unbridled optimism and energy, “beginner’s mind,” lots of free time and a connection to what’s new and cool.

As a 40-something, you’re supposedly stuck in your ways, not hungry, time-crunched and too focused on why something won’t work rather than why it will.

But my experience has been different. Besides “working smart” as opposed to just “working hard,” there are a lot of advantages I didn’t see coming.

Read more at Inc.com

Source: Dave Hersh

10 Questions for Finding Your Next Killer Product


It’s nice to have friends who are brutally honest with you. Say, for example, you abuptly switch from Banana Republic outfits to cowboy boots, a leather bomber jacket, and skull rings. Your friends should be first in line to intervene and let you know that it’s not working.


That kind of honesty is what you want in product feedback at the very early stages of a company. Most of us go out to “friendlies” who, not wanting to offend, tell you what you want to hear about your product (“I could see how comparing my cat’s personaliy to other cats in my area would be quite useful”). But that misdirected kindness will only cause wasted effort over the long run.

Read more at Inc.com.

Source: Dave Hersh

How to Kill Your Company in Order to Save It

Remember that movie 127 Hours? You know, the true story of Aron Ralston, the climber who had to cut off his arm with a jackknife in order to live? (There can’t be that many movies with that pitch.) As founding CEO at my previous company, I was faced with a significantly-more-creampuffy version of that dilemma back in 2006. We were churning out a profitable $9 million annually in sales and growing at 50 percent a year. Things were peachy. I didn’t know it yet, but I would have to kill off our entire business in order for it to survive.

Read more at Inc.com.

Source: Dave Hersh

How Strong Company Values Lead to Success

I’ve started posting my blogs on Inc.com. I’ll still do some posts solely on this site, but primarily will be posting there, with teasers to the posts on this site. This is my inaugural post. Hope you enjoy.


“What do you mean “passionate”? Stalin was passionate. Would we hire him?”

It was 10 years ago and I was CEO at my previous company. I had been called out by an employee on one of our core values of only hiring “passionate” people. I fumbled my way through an excuse, but they were right. We had done a great job with a purpose and vision, but the values were vague, trite, and ultimately useless in decision-making or inspiring people. It was like asking the contractor working on your house to “make it more interesting.”

Read More…

Source: Dave Hersh

Stressed to Impress: Don’t Get Derailed by Insecurity

Originally posted on FounderDating


I couldn’t sleep a wink. I was pissed. It was ten years ago. I was the Founding CEO of my last company (Jive Software) and was attending one of the many navel-gazing, Insertbuzzword 2.0 industry conferences.

That day, I talked to a “friend” who was the CEO of a company in a related space. With all the subtlety of a Sicilian stuck in traffic, he let on that his company was going to do in sales that year. And it was twice what we were going to do. I couldn’t believe it. I had worked so hard to crank out our revenue engine. And now we were getting passed. I couldn’t let it go. I decided to get hyper-focused on tripling our sales number for the next year and surpassing that Tool and his company.

Problem was, the whole idea of comparing myself to some adjacent company was ridiculous. Never mind that we had just moved the company from New York to Portland, hired a brand new team and bootstrapped the whole thing. I felt like I was losing a race in my mind, and I obsessed about it. Which was ridiculous. I might as well have been losing sleep over the Bennifer breakup (this was 2004 mind you).

Looking back on that period, it seems obvious: There’s nothing wrong at all with being passionate and focused on the next mountain to climb. The problem for me (and I suspect many first-timers) is that underneath that obsessive focus is intense insecurity that clouds judgment.

dog with frisbee quote


In the early days the misguided motivation was wanting to hire superstars. Then it was big sales numbers. Then it was raising capital from a top firm. More growth, board members, positioning for an acquisition, IPO, blah, blah. Anything impressive.

By themselves, these big goals are not really a problem. But if the outcomes you seek come from an insecure place of wanting to seen and be impressive, you either a) focus on the wrong goals, or b) neglect the work that best supports those desired results for those outcomes themselves.

Some examples of how the insecurity derailed me along the way:

  1. I took shortcuts to the goals. For instance, hiring people to do big deals but who, in my gut, I knew weren’t a cultural fit (and who ultimately blew up).
  2. I made it difficult for employees to confide in me because I had a hard time hearing anything but progress.
  3. I had a hard time enjoying the ride. You always feel like a better life is right around the corner, after you hit your goal, which is never the case. If you don’t hit it, you get deflated and feel like you’ve lost. And if you do, you realize it hasn’t changed things much and you sit in a vacuum while you find something else to take its place.

I see this insecurity in a lot of first-time entrepreneurs who want to prove themselves. Not only in their bragging about investors and customers, but even the way they think about the business. Like putting an “Exit Strategy” slide on a pitch deck. Seems innocuous, but what it often says is that the entrepreneur is unnaturally focusing on the outcome, likely because they equate it with their own worth as an entrepreneur. The reality of “exits” is that opportunities will abound if you build a great company, but focusing on the exit is the tail wagging the elephant. And it’s only going to cause you and your company pain along the way.


This time around as a startup CEO, I’m trying to save myself the pain. Knowing where you’re going and having Big Hairy Audacious Goals is important, but checking your ego and building out systems and processes form the basis for greatness. Focusing on things like:

  1. Doing amazing work every day. “Leaving it on the field”.
  2. Building out the infrastructure to keep your customers thrilled and your employees thriving.
  3. Becoming a true servant leader who is “cloaked” in the needs of the business.
  4. Thinking about process and system goals more than your big company goals, and celebrating those successes along the way.

Thanks to a little help from friends and colleagues back in 2004, I ultimately realized that trying to triple sales to one-up another company was not the move of a stable leader. Over the next few years, we built out a pretty rugged framework for business planning that put the needs of the business and the process goals up front. If we got all the that stuff right, sales would follow.

Usually people who preach to me about being “in the present” and “the journey not the destination” make me want to punch them. Especially non-entrepreneurs. But I’m chilling out in my “over 40” years, and now realize there’s some truth in that overused maxim: fully immersing yourself in the work itself, separating your ego from the equation and focusing on systems and process goals ultimately leads to better outcomes…and a healthier relationship with your company. You know, more like Ben and Jen.

Hot Tub Tithe Machine: Pledging Half of What I Make

Tis the season for come-back stories: It’s a Wonderful Life, A Christmas Carol, some new Sylvester Stallone vehicle. So as per holiday tradition, here’s my rumination on how to do better as a CEO/colleague/human the second time around.

Along my journey to find meaningful work, I struggled a lot with whether to work on a nonprofit. It seemed like the right thing to do, and I wanted to make a difference. I spent a chunk of time in the sector as a board member and volunteer, and worked diligently on learning about different causes.

But something didn’t feel right. Philanthropic work was meaningful, but felt a bit like playing a different sport than what I was used to in the for-profit world. And I wasn’t ready to give up on my game just yet, nor did I feel compelled to work on one specific cause above all else.

He picked up the ball and ran

Still, I wanted to do some good in the world and create some kind of legacy that mattered. Would working on another company mean I was selfish? That I was failing to achieve my legacy? Was I a lesser person? Was there a way to make it all work in harmony?

So with the clock ticking on my continuing search, I made a decision: no matter which gig emerges on top, the money I make will be subject to tithing. My pledge:

51% of what I make from this venture will go towards a foundation to support children’s education.

Having been inspired by colleagues at Andreessen Horowitz, who pledged 50 percent of their earnings to charity, and Warren Buffett’s Giving Pledge (for people in the wealth stratosphere), this felt like the right path: I get to keep playing my favorite sport, and also get to help others if the company does well. My pledge became 51 percent because it’s in the majority. And my one-upper personality wanted to at least win on percentage, since they’ll destroy me on the actual amount.

51% of who-knows-what may be a small contribution in the scheme of things, but it feels right and hopefully has some ripple effect. As one of the characters says in Hot Tub Time Machine (a more recent second-chance movie): “One little change has a ripple effect, and it affects everything else. Like a butterfly floats its wings, and Tokyo explodes, or there’s a tsunami, in like, you know, somewhere.”

My mother taught me something about ripple effects. She was a long-time special education teacher whose passion, dedication and optimism were a huge source of inspiration. Often, she was the only one who didn’t give up on her students, and instead created the environment for them to become their best possible selves. One of my closest friends from high school who worked with her as a teacher said: “She would work with the toughest and roughest kids and give them a soft place to fall with no judgment. She would even feed the ones that didn’t get breakfast. She was worth 10 regular teachers.”

If any other second-time, venture-backed founders want to join me with the same pledge, regardless of the cause you support, I’ve already bought the domain 51Club.org. Raise your hand, and we’ll get our own handshake and hats. And maybe give those fancy-pants Giving Pledge people a run for their billions in softball.

The purpose of this blog is not to brag or fish for compliments from readers (but you know, if you really want to say something…) I am merely sharing the details of my own journey because your engagement helps me hold myself accountable – and perhaps the ramblings can be helpful to others along the way.

I’m thankful that we live in a time when giving is becoming a bigger and more common part of the conversation and financial equation. The greedy and self-preserving tone set by early American entrepreneurs like J. Paul Getty who said, “If you can actually count your money, then you’re not a rich man,” seems to be drawing to a close.

I’m more drawn to Churchill who said, “We make a living by what we get, but we make a life by what we give.” Here’s hoping this second chance is a lot more givey than Getty.

Happy holidays.

Catcher in the ROI: Bringing Back Workplace Mojo

Have you ever watched a friend or former colleague lose their mojo in their work? Their fire and brimstone replaced with dull malaise. Their struggle to summon the energy just to talk about their company. It’s like a deflated clown balloon – there’s still a smile, but it’s sad and misshapen.

After witnessing this condition a lot lately, and having fallen victim to malaise in my own life, I started thinking about how to protect against it. Whatever I do next I want to create a culture of meaning, where people can stay challenged, alive and on their game – avoiding the death march of working with people they don’t trust or like, on a problem they can’t stand.

prison yard - Version 2

And I think you can do it without burning people out. I’m no longer in my selfish 20’s with nothing but time on my hands, so the challenge is to create a place where people are on fire, but can still maintain close relationships with friends and families and achieve equal or better financial success (except for any employees in their 20’s – they should be pulling all-nighters).

While many people will dismiss this thinking as the ramblings of a sun-burned ex-CEO too long out of the chair, I’m convinced there is a path that is both authentic and practical for achieving the proverbial “marathon, not a sprint.” Something between naive, feel-good HR sound bites and salty business advice with no magic.

The underlying question: Is great work culture solely a by-product of unbridled success, or does success come from great culture? Is it possible to see a return on investment (ROI) from investing in collective meaning that pays dividends throughout the life of the organization?

In pursuit of this work culture nirvana, I came up with the following personal tenets for my next gig. Taken individually, most of these points are about as original as an NBC sitcom plot, but together, they serve an important role in defining my next organization.

  1. Start with Purpose. Even if you’re not curing cancer, find a way to connect day-to-day activities to improving lives and helping people. Ensure colleagues understand the larger, human story behind what they’re doing. Great companies not only help the world, but provide a context in which the employees can become great in the process.

  2. Win. Pizza Fridays and foosball tables are useless if you’re not beating goals and winning. Too many companies are busy looking inwardly to understand their “culture” instead of focusing on the biggest contributor to that culture: success.

  3. Money Follows, Never Leads. Stay away from people driven primarily by money. I don’t want colleagues looking for “a job,” nor does anyone want to be part of a company run by bloated egomaniacs looking to buy their third Ferrari.

  4. Openness. As you can probably tell from this blog, I don’t just “open the kimono.” I burn it and run naked and screaming through town. While there is a small percentage of information you just can’t share, being open and honest about the rest of it builds trust and forms a tight culture.

  5. Teamyness. Ensure people feel connected and fired up, and that they’re supporting each other. Monitor. Hire diverse people, but ensure their values match up with the company’s, and be quick to kick out those who don’t further these goals (something like Willy Wonka’s golden egg machine for employees).

  6. Make ‘em Feel Wanted. At their core, people want to be accepted and valued for who they are. Celebrate the uniqueness of each person, even if that uniqueness includes stuffing their office with Charles in Charge posters.

  7. Celebrate Success: Some of my best memories are from victory celebrations. It’s rare in life to have those home-run moments after high school. Find ways to give people the chills because of what they’ve pulled off.

  8. Give Back. Connect work life back to the community as a whole (stay tuned for an upcoming blog on this one).

This pledge is easier to pull off in the early days when you still have a small, collaborative team. It gets much harder as a company is successful and scales. All the more reason it needs to be part of the fabric (values, mission, goals, tools, conversations) of the business from day one.

Ironically, in thinking through this problem, it dawned on me that helping those superstars who have lost their mojo is a source of meaning for me. Like Holden Caulfield’s eponymous metaphor where he wants to be a “catcher in the rye” to save children from the pain of adulthood, I find myself wanting to help people avoid a meaningless existence in the workplace and create the context for them to come alive again. I guess that’s the air in my clown balloon.

From Paralysis to Purpose in 90 Days

Recently, I challenged myself to commit to a gig by February 1 (see timer courtesy of Crushpath). My readers sent a lot of great feedback, questions…and a few very concerned head shakes. Some wanted to understand how I’m narrowing and filtering the options so that I’d be sure my next step was the right one. So with full-warning that this post is a bit of a selfie, here’s a snapshot of my process.

Getting to Know the Older Guy

Prior to starting the 90-day timer, I spent some time on what gets me up in the morning. Earlier in life, motivations were pretty straightforward (beer, money, opposite sex, beer), but with age, they’ve become more complicated. After seeing a pattern of ex-execs jump at the next “shiny metal object” job that came their way, I decided to dig deeper in the hopes of avoiding the wrong thing.

In a society infatuated with the self, there’s no shortage of tools designed to help people understand what makes them tick: Enneagram (I’m a 3), Myers-Briggs (ENTP), What Color is Your Parachute (mauve). I was even given a set of purpose cards (worst poker game ever). You could get caught up running self-diagnostics for months, but I think it’s best to pick one or two frameworks that fit your personality. Ultimately I found the most insights by asking myself: 1) When do you feel the most alive and why? 2) What do you want your legacy to be? 3) Who do you “want in the boat” with you?

I’ll spare you the navel-gazing details, but what I learned was this: I’m at my best when leading a team of creative GNAKs (good-natured ass kickers) on an entrepreneurial mission where new technology can make a huge difference in people’s lives.

Clarifying and Learning

Once I had a sense of the goal, the process for attaining it seemed less Herculean. I listed out my “Must Haves” (e.g. creative control, dinner w/ family 4 out of 5 weekdays, intellectual interest) and “Can’t Haves” (e.g. long commute, board members who think they know best, overly crowded market).

I interviewed people with similar early careers, but different paths afterwards. People who had been founding CEOs, but had gone on to become venture capitalists, exec coaches, serial entrepreneurs, social entrepreneurs, nonprofit founders, whiskey-shillers, ranchers and confidence men (last one made up). I looked for people who shared my values and passions, and learned everything I could. Then I listed the most appealing options.

Extreme Narrowing

With list in hand, I jumped into a professional dating period that rivaled Warren Beatty in the 70’s. Lots of good people and ideas, but in Silicon Valley everyone wants to be CEO of their own thing. Also, it’s hard to commit to people you haven’t worked with before – and difficult to get two strangers excited about pursuing the same goals.

Realizing the process was taking too long and going in weird directions, I set the timer and committed to focus. Since then, I have become shark-like in my priorities. No meetings that don’t advance the goal. Always aware of my daily tasks. I even set up a war room in my office for managing priorities and scheduling.

War Room from Dr. Strangelove

War Room from Dr. Strangelove

Since then, I’ve only focused on options that get me excited. These could include starting something from scratch (company, social venture, nonprofit, fund), becoming “Founding CEO” for an early-stage start up, and even taking a shorter term executive role to help companies get to the next level (selling the company, raising a round, etc.).

I’m giving each opportunity a rank of 1-5 in three categories: Gut (do I just want to go do it?), Heart (am I emotionally drawn to it?) and Head (does it make sense to do it?).





Next Action


Sample Gig 1




Conversation with Phil K.

In-person working session

Sample Gig 2




Talk to EIRs

Sample Gig 3




Dinner with Veronica and Tom

Facilitating a meeting would be good path

Sample Gig 4




Need feedback from Steve

Option for shorter term work?

Crab Fishing




Rent boat. Sit in it.

For each line item, I drive hard to a decision. If the opportunity remains interesting to me, I’ll take whatever next steps are required to learn more to bring me closer to a decision.

The best filter I’ve found is to work directly with the team involved. There’s no better way to get to know the opportunity than rolling up your sleeves on something together. This is especially true for new careers – if you’re a mailman and want to be a hand model, best to try it out first.

Final Thoughts

I found it helpful to take time away from all the voices. Too much advice can cloud judgment, and often the advice is what those people would do in your situation, not thoughtful insights into your unique path. (But please keep your comments coming – I’m totally listening.) As a culture, we get so wrapped up in what other people think, it can be hard to find purposeful work. We put too much emphasis on personal brand and image over happiness. It’s a shame. Most people are too busy taking their own selfies to care anyway.

You can be as structured about this process as you want, but my experience is that the gut knows best. The more closely I listen to it, the better the options become.