Why I Do What I Do

I had a GroundWork mentoring session last week with a founder I’d never met before. For the first half, he was very engaged but was defensive and eager to explain why his startup idea was brilliant and how I was missing the point.

Then it happened. He was lost for words. His story wasn’t cogent and he came to see that. A switch flipped and he became humble and receptive. At the end, he paused for a moment, looked down and shook his head. Then he raised his head and thanked me for giving him “the most massive face full of truth” he’d ever gotten about his startup and himself as a founder.

In case anyone cares, this is why I do what I do — Startup Haven, the Accelerator, the Fund, mentoring, advising, all of it.

We, as founders, tell a lot of different stories about our startups… to investors, to employees, to partners, to our family. Those stories are necessary; but they don’t materially impact the ultimate success of the business… because they are pretty much never cogent, i.e., they just can’t stand against the rigor of reason or logic or time. There is literally no other thing that a founder can do to improve their probability of success than to build a cogent story. So I’m gonna keep trying to help founders do that as long as I can.


Independence Day is Entrepreneurship Day

Independence Day is the closest thing we have to Entrepreneurship Day.

I’m a geek about Independence Day and the Declaration of Independence. If you haven’t read the entire document, I encourage you to do it. (Be ready to goggle some word definitions.)

Certainly, freedom, liberty, equality and justice are fundamental elements of the DoI. That’s the stuff we all have heard quoted over and over and over. But that’s all in the just first quarter of document. There’s much more in there! Warning: baseball, hotdogs and apple pie are not mentioned anywhere. But what is mentioned is entrepreneurship.

If you read the other three-quarters of the DoI (the parts that are almost never quoted) you’ll learn the “why” of the DoI, i.e., the list of the “long train of abuses and usurpations.” That’s where you’ll find that one of those abuses/usurpations was:

“For cutting off our Trade with all parts of the world”

I.e., the King won’t let us do business. In the closing section of the DoI, only four things are listed as examples of the Powers that want; three of them are related to war and peace… the fourth is to “establish commerce.”

America’s trajectory toward the ideals of the DoI have been imperfect. But entrepreneurship has fared well.

Expanding your luck surface area.

Reflecting on what I’ve learned over 20+ years founding, mentoring, advising and now investing in startups, the most essential lessons seem so simple. Talk to customers, early and often. Iterate. Hire slow, fire fast. Spend every dollar like it’s your last. To name just a few.

None of these are particularly difficult. Every founder I have ever met could do these things if they chose to. But early entrepreneurs often do none of them. I certainly didn’t apply any of these lessons to my first startup. I was too busy learning why these lessons are important. Ouch.

When a grizzled veteran founder says she has lots of scars and arrows in her back, this is what she means. She learned lessons not by reading blog posts of listening to panel discussions. She learned through the ‘scars and arrows of outrageous fortune.’ If she gives you advice you don’t like, you would be wise to consider it carefully anyway.

Mostly, lessons get learned through experience, by suffering their consequences. But it is possible also to learn lessons vicariously, from others who have experienced them.

This is why the most important lesson I have learned in 20 years is this: every venture-scale founder should seek out other experienced venture-scale founders. For insights. For advice. For introductions. For the empathy and commiseration that can only come from someone who truly understands what it’s like to be a founder.

Virtually all of the very best help you will receive as you build your company will come from people you know — people you know right now and the people you will meet in the years ahead. In my experience, there is no better source of help for a venture-scale founder than other venture scale founders. Full stop.

So, the big, fat lesson is… go meet founders. Lots of founders. Consider it your mission to build your network with as many venture-scale founders as you can. And don’t just look to get help. Also look to give help.

Every time you meet a new founder, that founder expands your luck surface area. And you expand theirs.

This is the project of Startup Haven.

No North Star? You can fix that.

In the GroundWork Workshops, the first, fundamental question I ask participants is, “what is the next strategic milestone you and your team need to hit in order to move the company forward in a meaningful way?” The first answers founders give are usually to tell me their our 60-day plan to increase sales. Or that they want to get to 100,000 customers. Or that they think they need to raise a round of funding in January. Or that in 12 months they want to be at $2M ARR. Or that next year they’re going release a new version of their product, open a new market and build out a professional sales team.

These are all real-life examples from founders I’ve spoken with over the past two years since we launched the GroundWork accelerator. All of these are wrong answers. None of them are strategic. None of them are within in a meaningful time frame nor tied to a specific date and time. None of them express what gets unlocked if/when they are achieved, a fundamental feature of strategic milestone.

If you are a venture-scale startup, the a correct answer can (and should) be stated in the form: “By {specific date and time 4 – 6 months out} we will achieve {single, highly-quantified objective} by doing {list of the most important tactics necessary for success} by doing so we will unlock {description of what next important milestone becomes available to you.}

For example:

“By April 25th at 5pm PST (six months from today) we will increase our MRR from $8k to $40k by focusing all of our efforts on quantitative marketing channels to acquire 1.5 new $1,000/month customers per week. By doing so we will reach a sustainable cashflow-positive runway, enabling us to raise a favorable round of funding to fuel our growth to $2M ARR.”

Determining whether this milestone is actually cogent requires a thoughtful and disciplined process of considering your available resources, determining the most important next achievements that you could reach with those resources, identifying what must be true (quantified assumptions) in order to reach that milestone and building a cogent plan that takes into account your most precious and scare resource — time. But none of this is hard. Every single founder is capable.

But there is no Startup Police. You’re not required to have a cogent milestone. It’s certainly possible to be successful without having one… and a next one… and the next. But one wonders… why would you not want to have one?

The right milestone gives you and your team a North Star, that one thing(s) that keeps everyone moving in the same direction along the shortest path. Your North Star helps you know when you’re spending your time, money and talent on the right things… whether you’re getting distracted… whether you’re making meaningful progress. In short, a North Star increases your chances for success.

If fundraising is in your future, there is perhaps no stronger signal you can send to investors than making consistent and meaningful progress toward a milestone that you can articulate as the right next place the company needs to be. The diligence process is essentially reverse engineering the story you tell them to see if it’s cogent and then correlating that with the execution they see.

Startups are chock full of uncertainty and ambiguity… and opportunities. The job of a founder is to sort through the opportunities to discover the right path forward and then execute the hell out of it. Nothing in the entire universe can help a founder do this better then identifying their North Star and building a cogent plan to reach it.

Why advising very early startups is irrational… and what to do about it. 

Over the past decade I have had the honor to mentor and advise many, many dozens of startup companies and startup founders. Companies and founders are not the same thing. Besides the obvious differences, also consider that startups fail much more often than founders. Sources often disagree on the actualy percentage of startups that fail. You pick your own number — mine is somewhere north of 90% and south of 96%. Yeah, startups fail a lot. And when startups fail, their done. 

Not so for founders. Many founders (probably most of the “good” founders you know) pick up the pieces, consider the lessons and get to work on the next startup — sometimes quickly, sometimes after recuperating at a Big Co while they reflect on the lessons learned and replenish their mental and financial stores.

In the very earliest stages of a startup (pre-product, pre-revenue, pre-cofounder, pre-funding, pre-everything) advisers are not (or at least should not) spend their time based on some calculus of the quality of the startup business or the outcome it will achieve. The risk adjusted value of time spent with startups at this stage is approaching zero, i.e., the failure rate of these startups is closer to 100% than the average failure rate of ~93% — these are the startups that help raise the failure rate amidst all the other startups that succeed. 

This is a good time for a personal point of clarification. When I advise founders at this early stage, I’m not motivated by my financial upside. I’m not putting the 10,000 – 50,000 stock options I receive in a spreadsheet and calculating the IRR on my time spent. 

The amount of time you would have to spend advising companies at this stage to make it financially justifiable would surely suck you dry of every spare minute and make it virtually impossible to get your own stuff done. I’m also not looking to sell them anything. Nor I’m not looking for a job. 

If, as an advisor, your motivation is to sell the startup something (now or eventually) or if you are looking for a role, then there could be a rational financial justification (sometimes along with a commensurate conflict of interest) to spend your time with very early founders. But if you don’t have some alternative financial interest in working with a very early founder, then there just is no rational financial justification to spend time advising them. There are, however, some irrational justifications.  

Speaking for myself (and others I know in the community), I do it because I want to help the founders, those courageous people taking on the herculean journey of building a company from scratch. I have taken that journey several times myself and I have benefited greatly from the generosity of more-experienced folks who helped me along the way. I do it to give back.

I also do it because I simply love spending time with smart people driven by a vision to solve problems in innovative ways. If you’ve never done it, you ought to try. It’s incredibly satisfying. 

Finally, I do it because I feel like I should… kinda. In his book, Startup Communities, Brad Feld aptly observes that long-term commitment is essential to growing and sustaining a vibrant entrepreneurial ecosystem. 

[For those looking to help build a startup community] the goal is to start finding the other entrepreneurial leaders who are committed to being in your city over the next 20 years.

I co-founded my first startup in 2000 but I didn’t become active as an organizer and mentor until 2006. So by the Feld-ian Framework, I will have met the community-commitment threshold by 2026. 🙂

I understand and I concur with the message Brad was delivering — building great startup communities requires work by real people and it doesn’t happen by accident. It’s sensible to think that longevity and continuity among of those contributing to the community is an intrinsic asset to that community.

But I don’t claim any sort of altruistic credit for having ended up here. What I do is not saintly. I did stuff I thought was interesting, fun and helpful and the Fates made it possible for me to do it for a long time. If anything, it’s a kind of disease. Over the years, some of my own mentors have strongly suggested that I should reevaluate my approach to mentoring and advising because “it’s just not worth it” and “it could impact the success of your own projects.” But I haven’t found the antidote yet. 

But this piece isn’t meant to be an episode of “The Bob Show.” My interest is in exploring the relationship between very early startups, their (often first time) founders and the advisors who spend their time with them. 

A core question on this topic: if spending time with such early-stage founders is financially irrational, then why take stock options at all? Why not just help startups by way of Advising’s vagabond and uncompensated cousin, Mentoring? Doesn’t mentoring get you all the irrational benefits you’re seeking without all the messy paperwork and commitment?

It is an irony that truly being helpful at this early stage requires making a commitment to being informed, engaged and accessible, i.e., exactly the kind of help that good advisors would be irrational to offer. But that’s what advisors at this early stage sign up for. Trajectory. 

Mentors make no such commitment and, as such, are often constrained to providing drive-by advice based on tactical problem solving. While this sort of help from experienced, knowledgeable and connected mentors can be extremely valuable, it is of a different category from the sorts of help provided by committed advisors with a trajectory perspective. 

Along with this trajectory perspective, good advisors also bring patience to help founders learn and improve as founders as opposed to principally satisfying the startup company’s immediate needs of the day. 

For founders at the very earliest stages of their startup, offering stock options to an experienced and committed advisor is not a financial proffer; it is an acknowledgment of the founder’s respect for the value of the advisor’s time and their commitment to the founder’s personal entrepreneurial journey. 

As a founder’s startup makes progress and gets farther from pre-product, pre-revenue, pre-cofounder, pre-funding, pre-everything, the expected value of a startup’s outcome increases and any given advisor’s rationale and motivation for serving as an advisor at those later stages also changes — the Benjamins seem reasonably within reach. 

As each inflection point approaches, the experimental nature of the founder’s idea, product, customer, company, outcome diminishes and execution becomes the order of the day. The advisor role evolves from advising a founder (a person learning to be a founder) to advising a startup (a company looking to grow.) The startup’s outcome becomes less ambiguous and less risky… and advisors are much more easily justified in spending their time with the startup. But early on, there is no clear story to tell about how the Benjamins will ever arrive. And nearly 100% of the time, the Benjamins never do arrive. Building a company is hard. 

Beyond acknowledging the value of an early advisor’s time and the utter unlikelihood that the founder’s first startup(s) will be successful, advisors often just want to play the game along with the founders. And that’s healthy and fair.

In poker (which I know a thing or two about), everyone in the game puts their assets at risk and everyone has something of value to gain. In startup-ville, we refer to this as having “skin in the game.” As it turns out, having even just a little bit of skin in the game (even with very little probability of winning) makes a materially positive difference in how the players conduct themselves. 

Poker fans will recognize the term “free roll,” a poker game played where no one risks anything, i.e., everyone gets a free stack of chips to play with. These games are terrible and knowledgeable or experienced players will not want to participate because no one “plays right.” With nothing at all at stake and nothing to gain, players show no discipline, no strategy, no focus; it just doesn’t matter. 

When a sufficient number of players at a game are not playing “good poker” then even those who would otherwise want to play well simply give up because, as it turns out, it’s impossible to play poker well in a game where the other players don’t care about the outcome. But if you have each player drop a tiny little 10-dollar bill in the pot, all of a sudden the desire to play well abounds. Caring about the outcome, even in a small and seemingly insignificant way, makes a meaningful difference. Giving advisors options gets their skin in the game. It makes them care about the outcome in a different way. It makes them a player too. 

But to be clear, this is not about making advisors feel like they could make a bunch of money if the startup “wins.” If anyone ran the numbers on the risk-adjusted value of those options, they would quickly realize the folly of that notion. This is about connecting the advisor to the founder’s success and making them feel part of it. 

From all this, some interesting conundrums arise. What happens to the advisor who commits their time to a first-time founder when that founder’s company fails and s/he immediately starts the next company? The advisor agreement was with the first startup company, not with the founder. So is the advisor just out of luck if the next company has some success? Legally, the answer is yes, she’s out of luck. But consider the following, more-detailed analysis:

A first time founder, Mark, has an idea and some programming skill. He builds CoolWidget.com but hasn’t yet figure out how to make it a business. Mark meets an experienced and knowledgeable founder, Beatrice, who’s willing to help. They enter into an advisor agreement. Beyond tactical and strategic advice, Beatrice serves as founder coach, helping Mark understand the broader lessons and implications of the tactical and strategic decisions he’s making. Mark thinks highly of Beatrice and is grateful for her help and their relationship. 

CoolWidget.com was a good idea but doesn’t go so well. Turns out that lots and lots of really good ideas are extremely difficult to fashion into good businesses. At about this time, Mark meets Alice, another solo founder with programming skills who built SuperTool.com. SuperTool.com is also a great idea but Alice also hasn’t found commercial success yet. They decide it would be better if they join forces and work together on just one of their startups. Beatrice meets Alice and they all agree that Beatrice would be a great asset as an advisor for whichever company they decide to pursue. Beatrice helps Mark and Alice think though their options. It’s a close call, but Mark and Alice ultimately agree that Alice’s startup, SuperTool.com, is a more-compelling story; Mark sets CoolWidget.com aside and joins SuperTool.com as co-founder. Beatrice continues her role as an advisor for SuperTool.com.

Alas. Building startups is hard. SuperTool.com is truly super, but it struggles to get traction with customers and investors. Failure is the norm for startups so this is not an unusual or even surprising outcome. But the product has been evolving, getting better and aligning with what customers really want. Since Mark and Alice we able to stay in the game as long as they did, they are seeing new opportunities.

A final pivot ensues. This one, GreatPlatform.com, looks good… maybe even great… it could be “the one!” The transition from SuperTool.com to GreatPlatform.com is contiguous in time and team but Mark and Alice go dark for six months while they are heads down building the MVP. Beatrice notices that Mark and Alice haven’t communicated in a while so she pings them: “How are you guys doing??” Mark and Alice: “Thank you so much for reaching out and checking in! We can’t wait to show you what we’ve been working on. Let’s connect soon.” 

Finally, Mark and Alice emerge triumphant. Mark, Alice and Beatrice meetup and, seemingly, pick up where they left off. The new product looks great. In the coming weeks, things move fast for Mark and Alice. Investors are showing interest, customers are lining up. The company gets a new name and a new corporate entity, flushing the previous cap table and all of the baggage of legal agreements.

Mark and Alice’s newest advisor, Mr. Shiny Neu, tells them that they should cut ties with all previous advisors unless they can bring three VCs and a big customer to the table like he did. It’s unclear whether Mr. Shiny Neu would have spent 5 minutes with Mark and Alice over the previous three years, let alone whether he could have gotten even one VC and a small customer to pay attention in those early days when CoolWidget.com and SuperTool.com were fundamentally unfundable.

So they do it. They have a call with Beatrice letting her know that her previous support in getting them to where they are now is no longer a legally binding relationship. “Sorry Beatrice,” they say, “you’ve been great but the company is technically a new legal entity and the product is kinda pretty sorta different and we’re badasses now so we don’t need you anymore.”  

Did anything go wrong here? Or is this just one of the many possible fine and natural outcomes, perfectly in line with the reasonable expectations of founders and advisors and squarely within the letter and spirit of the agreements?

How should Beatrice feel about this? After all, when she started the engagement, she wasn’t doing it “for the money.” And now she’s clearly not gonna get any. So mission accomplished, right? If the answer is “no, that wasn’t the mission,” then how should she change her ways to help prevent this from happening again? Should she just stop spending her valuable time helping nascent entrepreneurs?

How should Mark and Alice feel about this? After all, there is no legal advisor agreement in place for the new company so they cannot have breached any contract, right? Beatrice doesn’t have a legal leg to stand on, right? And they seem to kinda feel bad about it, so that shows they are not sociopaths. In fact, they tell Beatrice that they really like her as a person, are grateful for her time and tutelage and still want to be friends. But, “hey”, they say, “it’s just business.” Beatrice hears, “thanks for everything… now screw you.”  

As a philosophy grad, I was trained to decompose, analyze and understand all of the possible arguments and counter arguments for any given claim. So I can imagine smart and experienced folks disagreeing about what happened here — whether anything was legal or illegal, just or unjust, ethical or unethical, wise or unwise, smart or stupid.

Whatever your take, I have a proposal for your consideration. 

Pro Rata Advisor Agreement 

This agreement would add clauses to a standard advisor agreement that would provide advisors with rights to preserve their vested option base in a successor startup founded by a materially similar founding team. Of course, the agreement needs to be fair to both sides and should not create such an onerous obligation by the founder that it could interfere with other relationships the founder may need to forge later (e.g., bringing on co-founders, investors and other advisors.) Neither is the objective to make a founder into an indentured servant to the advisor. But I think that these constraints can be satisfied. The parameters of the agreement would certainly include:

  • Whether the advisor materially breached the prior agreement.
  • Composition and continuity of the successor founding team. 
  • Length of time between the demise of the precedent startup and formation of the successor startup.
  • Pro rata portion of the advisors equity ownership to be transitioned.
  • Requirements and terms for the advisor to maintain their role and duties as an advisor. 

Bullet points are simple… legal agreements are seldom simple. So there is work to be done here. But is this a basically good idea? Even with a pro rata agreement in hand, it strikes me as still financially unjustifiable to advise super-early founders. But at least everyone involved would be treated fairly. I would be grateful for your thoughts on the notion of a pro-forma advisory agreement as well as any other ideas you have on the topic. 


Strap a Spreadsheet to Your Passion

(Originally appeared in GeekWire)

I’ve met a lot of really bright engineers and entrepreneurs who I think could do great things if they strapspreadsheetpursued a big, interesting problem in a big, interesting market. But instead they get enamored of scratching their own itch, i.e., solving a problem they themselves have experienced and then didn’t find, didn’t like or didn’t even look for someone else’s solution to the problem.

What’s wrong with that approach?

There was a time when I would have said: “Nothing, it’s great.” And I still think it can be great. But I no longer think it’s definitely great. Regrettably, too many otherwise really, really smart people believe that doggedly attacking their private obsession with great passion is THE way to do a startup.

Sorry. That’s just wrong. And it’s got me rethinking the role and value of entrepreneurial passion.

We’ve all heard the stories of entrepreneurs who experienced a problem and then attacked the problem, fanatically, until they figured out a simple solution. They built a prototype, raised seed capital, worked hard and then sold to Google for a ton of cash.

Some of the stories include apocryphal accounts of entrepreneurs who believed against all odds that their idea was meaningful and would amount to something, even in the face of dozens and dozens of investor rejections, colleague admonitions and the cold shoulder from customers.

See, the myth goes, all you have to do is passionately pursue a solution to a problem you’ve experienced and you’ll be rewarded. Believe in your dream. Prove them all wrong. Never give up. Bullshit! There are two major reasons why passion alone for your idea can be dangerous.

1) Your IDEA doesn’t know a damn thing about business.

There are countless ideas that I, you, and everyone else, have that just do not warrant spending any more than “hobby time” on. If you want to create a business (which I read somewhere is the point of being an entrepreneur) solving a problem isn’t, well, the problem.

Solving a problem in a way that creates value sufficient to justify someone paying money for the solution (an amount of money sufficient to sustain and grow the business) is the problem.

Investors have a nose for this. And, if your problem doesn’t smell like one that people will (eventually) pay enough money for, then they are unlikely to invest. And if you’re gonna bootstrap (i.e., not take Other Peoples’ Money) then you need to get QUALIFIED external validation of your business because you won’t be getting it from your investors.

Your wife, your best friend, your co-worker, your aunt Judy and your neighbor are not qualified to give you advice on whether your idea might also be a viable business.

If I were going to bootstrap a new business, I’d still look to talk to investors for feedback on my idea as a business. Short of that, find some serial entrepreneurs to talk to, preferably ones who have lots of arrows in their backs.

2) Your PASSION doesn’t know a damn thing about business.

Passion is by definition not rational; and it’s certainly not business savvy. I would go so far as to say that passion (a close cousin of faith and love) is blind. Be careful. I get a little shiver up my spine whenever I hear an entrepreneur justify what they’re working on because it’s a problem they’ve experienced.

It’s as if the mere existence of their passion is what is going to make the difference in their success or, worse, that their passion is what qualifies them to solve the problem in the first place.

The reality is that mere passion about an idea is not a good reason to pursue it; nor is it an indicator that you’re capable or qualified to solve the problem you experience. In fact, the more passionate you are about an idea the more vigilant you should be about getting QUALIFIED third-party validation that your idea could actually be a business.

I don’t mean that you shouldn’t trust yourself. But I do mean that you should not trust an irrational, emotional drive to solve a problem as evidence that the problem is worth trying to build a business around.

Even if there is a business that could be built around solving that problem, that doesn’t mean that you are the one who can solve it. If you get some business validation around the idea and it is in the realm of possibility that you could build that business then your passion may turn out to be an asset.

Now that I’ve railed on passion, I have a confession to make.

I am a dangerously passionate entrepreneur. I also believe that passion is a tremendous asset to entrepreneurs. I would characterize it as necessary, but not sufficient. So what’s passion good for?

Passion can be the spark that gets you going. And it can be the fuel that keeps you going. It will keep you awake late nights. It will inspire confidence as you build a team, raise capital and engage early customers.

There are better things to be passionate about than scratching your own itch. Be passionate about building a great team, passionate about designing a great product, passionate about delighting your customers, passionate about making a difference in people’s lives, passionate about finding and scaling a sustainable business model.

These passions will serve you well whether you’re solving your own problem or someone else’s problem.

But passion just about your personal experience is actually shaky ground.

If you’re so passionate about solving your own problem, then you risk missing some really important things. For example, your market might share your problem too. But they might think about in a very different way.

If your passion about your solution to the problem is incongruous with the way your potential customers think about the problem then you’re in for a tough run. Beyond that, lots of startups end up pivoting their product/market/business pretty substantially away from where they started. This is healthy.

But, if you’re obsessive about solving your problem your way, then you may just miss the real market opportunity. And, if you end up pivoting and land on a product/market that you’re not as passionate about, then you’ll have lost the motivation that got you started in the first place.

Passion may just keep you in the game when nothing else will. When the dark days come (as they usually do) it can be hard to keep going. In the dark of night when you’re running out of money and can’t make payroll, your competitors are beating you badly, you’re being sued by a former employee and 1,000 other things that suck, your passion for the business can keep you from returning that call from the Amazon recruiter.

A closing thought.

If we had to wait around for entrepreneurs, first to suffer from every problem worth fixing, and we had to wait around for the ones who were also passionate about fixing it, and we had to wait around for them to successfully build a viable and sustainable solution, then not very many problems would get fixed. And not very many successful businesses would be built.

If you personally experience a problem in a way that makes you passionate about building a solution then congratulations — you have a reason to think about whether there is possibly a viable business that is worth spending time on. Now, go formulate and test your assumptions about the problem, the solution, the market, the revenue.

Spontaneous Youth Entrepreneurship

So far, 356 heroes have stepped up to get Project Wise Walker within striking distance of our crowd funding campaign on Kickstarter. By any measure, that’s amazing support and we couldn’t be more humbled or grateful. But with less than 24 hours left to go and a 10% gap to close, we could use a few more heroes.

Here’s the link if you can help: http://rjc3.co/ww

Wise Walker really is a fantastic product. Every time I walk Lola I realize its value and I would seriously miss it if it were gone.  But there’s more to Wise Walker than just the best darn dog walking accessory ever made.  Wise Walker is also about youth entrepreneurship and a dad on a mission to release two powerful women on the world.  Here’s a story to show you what I mean.

One Saturday last year, about six months into our entrepreneurial adventure, Sarah and Annalise had their friend, Sehoya, over for a play day.

They were all in their bedroom playing quietly. As some of you parents know, that’s not always a good thing. I peaked in the door to check on them and they were all on the top bunk with a laptop computer and clipboards.

Their reaction to the intrusion was immediate and . “Dad! Go away!” “Get outta hear… this is private!” Very quickly scanning the scene I deduced that trust was called for and I just as quickly ducked back out. I let them know (talking through the door) that we would be heading over to Student RND soon.

Student RND was a hacker space for youth that has since shut down. But the team behind Student RND went on to expand the now-national “Code Day” program they had created at the space.

The plan for our day at Student RND was the usual: take some things apart, attach some wires to some batteries to see what happens, maybe build a contraption or two. Oh yeah, and cutting parts out of wood and acrylic on the laser cutter. 😉 Today’s special project was going to be a personalized wooden keepsake box for Sehoya’s birthday.

While I was getting the laser setup, the girls had setup chairs in a circle to continue whatever it was they had started in the bedroom earlier that day. They were intent on keeping their activity a dad-free zone. They had clipboards, so that’s cool.

Turns out, what they had been working on was their own business plan. They wanted to create the first ever large and exotic pet sitting service — tigers, elephants, turtles, snakes, giraffes, guinee pigs horses of course. The talked about the kind of facility they’d need (big) and what it would cost to build and run the business (a lot), what they would charge customers (enough).  It was the full meal deal and I couldn’t have been more proud.

It’s impossible to know today whether Sarah or Annalise will go on to someday become noted women entrepreneurs, creating a product or service that solves real problems and create jobs.

What I do know is that Annalise and Sarah as 12-year-olds are gaining an understanding of entrepreneurship that is preparing them to take on the challenges of entrepreneurship if they choose to. In the mean time, the lessons, skills, experiences and confidence that have come from Project Wise Walker has been an amazing gift for a father to share with his daughters.

I’m looking forward to sharing those lessons, skills and experiences with other families who want to explore entrepreneurship together. I can’t share the confidence; but trust me, it will come from within.

All the best,


Fun With Math — How My Daughters and I Are Making the World a Better Place

It’s not hard to find startups touting their mission to “change the world” by making it 4% easier to find a book you’ll love or  reducing the time it takes to add inane content to the webs from 40 seconds to 31 seconds.  No value judgement here… just an observation that “changing the world” may be a lower bar than you might think.  For all those book lovers who love to find books they love, a 4% improvement over a life time of reading is a worthwhile innovation.

One of my favorite “changing the world” stories is the one about Steve Jobs insisting that making the Macintosh boot 10 seconds faster would save dozens of lives. With 5 million users, Jobs claimed, that 10 seconds would equate to 50 million seconds… or dozens of lives. He got the math wrong but the idea was cool.

Thinking about the math of changing the world, I wondered about how much better my daughters and I were going to make the lives of dog owners through our Wise Walker invention. You can learn all about the Wise Walker at http://rjc3.co/ww (Hurry if you wanna get a Wise Walker… our Kickstarter project closes in about 50 hours, i.e., 9am PST on Tuesday, 11/25.)

So here we go… with correct math.

If you walk your dog twice per day, seven minutes in the morning and 12 minutes in the afternoon, that’s 6,935 minutes per year.

Assuming your dog gets his business done in the first four minutes on each walk, that leaves 4,015 minutes (~67 hours) of carrying that nasty bag around each year.

Your Wise Walker should last at least three years (probably a lot longer!), giving you 12,045 mins, or 201 hours of relief from handling that bag over 2,190 walks. At a $25 pledge amount, that’s 2/10 of one cent per minute of relief, or about one cent per walk.

If we deliver 400 Wise Walkers through our Kickstarter, we’ll bring 4,818,000 minutes of relief from carrying around nasty bags of dog “business” in just the first three years.  That’s something we can be proud of.  😉

Why I’m Teaching My Daughters Entrepreneurship

Like any dad, I want to do everything I can to prepare my young daughters, Sarah and Annalise, for the lives that lie ahead of them. This includes teaching them right from wrong, how to stand up for themselves, how to always act with integrity, the value of education, good eating habits, the importance of exercise and the many other valuable lessons of life.

I consider the lessons of entrepreneurship to be tremendously valuable as well. The reason is that my daughters will grow up in the United States. They will derive their livelihoods from within a highly competitive, technology-dependent, capitalist economy. The skills they will need to thrive map remarkably close to the skills that help entrepreneurs thrive.

Moreover, if the trend in entrepreneurship continues at even a quarter of it’s current pace, the opportunities available to those confident in the art and science of entrepreneurship will be tremendous.   The thesis is that by the time my daughters are 20-somethings, their experience and comfort with entrepreneurship could be a distinct advantage — maybe sooner!  😉

Sarah and Annalise are not relevantly different from millions of other kids who are also facing headlong into a new future where entrepreneurship will be a viable opportunity for so many more than it ever has been. Of course, not everyone will, or should, or can, become an entrepreneur — if everyone is a founder then not much work is gonna get done.  But if you have kids and you want them to have all possible choices available to them then, I propose, it’s smart to prepare them to understand and operate in an evermore entrepreneurial world.


We have been working together for more than 18 months on our entrepreneurial project and that project has resulted in a Kickstarter project for a pet product we developed together.

Here’s an incomplete list of some of the skills I think the girls are learning:

  • critical thinking, decision making and problem solving
  • team work and cooperation
  • public speaking
  • interpersonal communication
  • professionalism
  • how businesses are built and run
  • how technology can solve problems
  • how technology can cause problems
  • why design is important
  • what a spreadsheet is
  • what a financial model is
  • how manufacturing, fulfillment and order management works

Some of the impacts I’ve seen in my daughters through this entrepreneurial experience include:

  • increased confidence and self-esteem
  • responsibility and leadership
  • patience and perseverance
  • delayed gratification

Importantly, these skills, lessons and experiences are coming through actually doing entrepreneurship, not through lectures or text books.

confuciousI hear and I forget.

I see and I remember.

I do and I understand.

 — Confucius

I’m also on a mission to unleash two powerful women on the world. For me, that means making my daughters understand that they can do anything they choose to do… and that there’s nothing they can’t chose.  Seeing themselves create a solution to a problem and to see that solution become a real product brings with it the powerful message that “I can do that… because I did.”

Of course, this a powerful message for any kid to receive, girl or boy.  But I think it’s especially important for young girls to get this message, as there is clearly a gender gap in some of the most lucrative and rewarding careers in our economy, including technology, entrepreneurship and leadership.

I know this experience is having an impact on my daughters. I see it in the way they have engaged in the process and taken on the responsibility of the work. I hear it in the way they talk to others about the project.

No one knows if either of the girls will someday be startup entrepreneurs. Frankly, I don’t think it matters. The skills, lessons and experiences of entrepreneurship will be valuable to them both no matter what passion they pursue.

If you were to ask Annalise today what she wants to be, she will not say “entrepreneur.”  She will say “veterinarian”.  Sarah will say “professional volleyball player”.  And that’s how it should be.

Entrepreneurship is not something you do in a vacuum and it’s not something you pursue for it’s own sake.  If Annalise is to become a successful entrepreneur, she may very well do so by inventing a new medical device to help horses or launching a chain of on-demand, in-home vet care clinics or the Uber of pet transport services. Perhaps Sarah will be inspired to create the first VR sports competition platform or a DIY publishing platform for young writers.

Empowerment is not turning someone into something. It helping them turn into whatever it is they want to be.

The best part of this experience is that it’s a win/win no matter what happens because the quality time we’re spending together is all the reward that’s necessary for any of us. But preparing them to crush it in the real world is a great side benefit.

Fun with Celebrity Dog Poop

As my faithful readers know (both of you), I’ve been working with my 12-year-old daughters on a dog poop bag carrying product called Wise Walker.  Fantasizing about how great it would be to have a celebrity endorsement,  I Goggled “celebrity dog poop bag”.  I was surprised to find out that pics of celebrities carrying dog poop is “a thing”.  Even the Huffiington Post has a slide show.

A few of my favorite pics are below.  If you happen to know a celebrity with a dog (isn’t that pretty much all of them?) then be sure to let them know that they never have to be photographed carrying crap around ever again.



Ashton Kutcher


Charlize Theron




jessica biel ticle-0-19A47007000005DC-71_634x645

Jessica Biel


Anne Hathaway

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