Startup Lessons Learned This Week: The Power of ‘No’

Image for the Dasheroo Power of No article.As I mentioned in Startup Lessons Learned in the past couple weeks, we’ve launched our pricing and our billing solution. So now that we can actually charge people, we’re getting into sales discussions with agencies and larger companies who are interested in our business dashboards solution. It’s exciting!

That said, we just launched Dasheroo on May 5, so we’re still early on and we don’t yet have all the features and functionality that more advanced users like agencies or consultants want. Features like co-branding our app, dashboard exports, and user roles and permissions.

So, just this past week I’ve been in the unenviable position of having to say ‘No’ (more on that below) to several excellent prospects. “Do you have co-branding?”, “Can I export your dashboards to a PowerPoint?”, “Can I make this dashboard read-only?”

‘No’, we don’t have any of those features yet. Years ago I would have freaked out to not have a pocket full of “Yes” to respond with. I would have felt like a loser, and the pressure to close a sale now would have been immense.

But there are benefits of this powerful, and sometimes feared, word. Let’s take a closer look at ‘No’:

  • It shows some real honesty & confidence; people appreciate that.
  • You can sometimes turn a ‘no’ into a thank you, when the request sounds reasonable but you’re just not sure if you’ll ever get around to it. Occasionally we’ll receive feature requests than actually sound great, but not for the near term. So it’s not a ‘no’, it’s a “Thank you for your suggestion. This feature isn’t on our near-term roadmap, but I’ll get it in front of our product folks to review…”. And we do review each feature request we receive.
  • ‘No’ can often be communicated as ‘Not yet or ‘No, but…”, if that is an accurate statement. For instance, co-branding, dashboard exports, and advanced user roles and permissions are in fact on our near-term product roadmap. People will be patient if they believe that your goals are aligned and you’re open with them.
  • Sometimes a firm ‘No’ is warranted. In the case where one customer may be forcing feature demands on you that will not value the balance of your users, or is just something you feel strongly is not in your best interests. Jason Freid of Basecamp wrote a great article a few years ago, where he noted that a customer requested they provide Gantt Charts as part of their Basecamp project management offering. He duly noted that many other companies already provide Gantt Charts and it’s not something they will ever consider.

After several agency and larger company meetings the past week or so, the results are interesting and encouraging. People genuinely like our user interface, ease of use and pricing. That’s the core of our value proposition. So when we discuss upcoming features and functionality with these folks, we’re driving toward a mutually beneficial solution and inviting them to help define that solution. Plus, we’re often able to provide some short term workarounds in the meantime.

So can forms of ‘No’ actually get you to a yes? It’s looking promising, plus it ensures that we stay true to our product vision, which hopefully will benefit all of our users for years to come.

What’s your take on the pros and cons of ‘No’? Let me know!

Startup Lessons Learned This Week: Setting Our Pricing

Last week in Startup Lessons Learned I discussed the importance of establishing sales strategies on both ends of the business spectrum – from a strong ‘auto convert’ for the SMBs all the way up to big ‘ol enterprise types. What that means is this – folks that will pull out their credit card for a $19 purchase when electronically prompted, all the way up to negotiated contracts in the several of thousands of dollars.

So when deciding on your startup pricing strategy, there are so many important items to consider. But I’m going to focus on the 3 biggies we drilled into when setting our initial ‘auto convert’ pricing, as I feel they establish the foundation of a good pricing strategy. Here we go:

1) Your costs. Evaluate both fixed and especially variable costs. For us, the incremental costs of supporting each new user is relatively low. Our incremental costs get down to efficiently scaling the backend server and database costs, being very efficient with API calls to the 3rd party applications we connect to, and customer support. With a business freemium model like we have, incremental variable costs must remain low. For yours? Who knows, but start with your cost basis, and make sure you are very realistic on your costs now, and how they will change over time, especially if you grow.

2) Your competition. You need to be mindful of the competitive environment. Businesses are very cost-sensitive. Does that mean you need to undercut your competition? Not necessarily. First, try to understand your competitor’s pricing approach. What are they basing it on?  Is it per user or per ‘widget’? Figure out their pricing metric(s). If you can understand that you can shape your pricing to be a greater value. And that is really what it comes down to, to win the long term race. Value.

Note: Don’t get too crazed by just one competitor’s pricing. You could whip yourself into a frenzy trying to compete with it, and then they change their pricing the next day!

3) Your value. Here’s where your pricing strategy culminates into a successful business. Answering the question “What do users derive the most value from?” You can’t trick, cajole, or hold important stuff hostage, in order to drive long term profitable relationships with your users. And although price points are a huge consideration, if they are not based on ‘value realized’ it won’t matter.

Bottom line, here’s what we did for our SMB auto-convert pricing (I’ll talk agency and larger company pricing in a future post.)

Ou just launched business dashboard pricing

Our just launched business dashboard pricing!

  • Free! We call this our “Tall” pricing tier. We feel business freemium reduces the risk a business takes, and allows for rapid global adoption. Sharp folks like Mailchimp, LinkedIn, Hootsuite and SurveyMonkey have all proven this out. Otherwise, users are forced to make a pay/flee decision after a 14-30 day trial, and often these busy users need a longer period of time to derive value from a product. We felt that leading with a 100% risk-free offer satisfies my three considerations above,  provides a huge value, a competitive advantage and fits within our cost structure.
    • We’re big believers in really providing great value in the freemium edition. No stripped down bait-and-switch type stuff. At VerticalResponse (where a lot of us have experience from) we re-tooled the traditional 30-day free trial into a freemium.

Dilbert: Freemium Model Cartoon

  • No ‘per user’ pricing. We really deliberated on this one! Debated. Argued. Hell, I think I argued with myself on this decision! But at the end, we all came to agreement that our pricing should be more like Basecamp’s pricing for project management than Insightly’s per-user pricing for CRM. CRM tools like Insightly naturally lend themselves to a per-user pricing schema, but with business dashboards, you get some users that may casually log in once per month, others that log in daily. So why make people hesitant to invite that casual user?
  • Great conversion price points and clear value triggers. So, the next pricing tiers are Grande and Venti, tipping a hat to Starbucks. You want to achieve a couple things here. First, there are natural price points that tend to drive a conversion. As in our $19 Grande plan. Sure we could have priced at $23 or $16. But we’ve done enough testing in our (long) lives to know that we’ll get as many folks to pay us $19 than $16 (I’ll take an extra $3/month to invest in innovation), and probably drive 30%+ conversions than pricing a couple bucks over the magic $20. Same goes for the Venti pricing. Secondly, our value-add (triggers) are clear. It’s completely usage based. You consume more Insights, we hope it’s clear that you should budget a little more per month for that additional usage, and a couple more bells and whistles.

A guarantee? We’ll most likely change our pricing at some point. As we learn, instrument (we love Mixpanel!) usage, get feedback from our awesome users and add more features and functionality we’ll adjust our prices. But we plan on always treating our current users well, and offer ‘grandfather’ plans to them.

Oh yeah, why the caffienated pricing? It just seemed catchy and fun. Hopefully it’s clear to people, otherwise we may change those labels as well!

Startup Stories: Lessons Learned This Week

This is an exciting week! After several weeks of heads-down development and product work, we’re about ready to release our billing functionality. Maybe that doesn’t sound sexy, but to us it’s where the rubber meets the road…will people pay for Dasheroo? Many have said they will be happy to, so let’s see.

But that’s not the startup lessons learned this week; it’s obvious when you are starting a business that you need to charge for your service. But there’s actually several lessons that this billing project has taught me, and I’m going to focus on a key one now, one that I learned at my last start-up and one that is being reinforced in my experience at Dasheroo.

Dasheroo's diversified sales strategy.

At Dasheroo we’re planning on diversifying our sales to different targeted audiences…are you?

And that lesson is that even with an SMB-focused offering, there’s a huge importance of establishing ‘larger company/enterprise’ sales efforts at the get-go. If that seems contradictory, hear me out. Here are my top 3 reasons we’re pursuing this strategy at Dasheroo:

1) Cash flow: In a business freemium model like we have, it takes a lot of $19 per month transactions to make a dent in the cash burn of our business dashboards company. Sure, it’s vital to build what we call the ‘auto-convert’ side of the business and establish our conversion metrics so we can begin modeling out what the business will look like 3-5+ years down the road. But I was reminded of my experience at my last start-up, VerticalResponse, of the value in generating cash NOW.

Similar to Dasheroo, VerticalResponse catered to the SMB market, providing a self-service email marketing platform. Most users paid less than $15 per month, and we knew we needed to offset our cash burn faster than those smaller sales could support. So we targeted companies with large email lists – e-commerce companies for example, that were happy to pay us thousands of dollars per month for the great email deliverability and VIP support we’d provide.

2) Diversification: Although the global small-midsize business market is well diversified with tens of millions of companies – we already have users in 100 countries from a gay pride foundation in Montenegro to a beauty school in Indianapolis to a dev shop in Guadalajara. But I’m talking more macro-level diversification from a sales perspective. Larger companies behave differently. They tend to buy on an annual vs. monthly basis. They tend to like ‘per user’ pricing and VIP support. All items that provide value to our larger customers that we are then able to charge a premium for.

3) Long term sustainable growth & value: This is an issue that really surfaces after you have achieved a level of success selling to SMBs. The spigot of early adopters tend to dry up a bit over time, and it becomes increasingly difficult to sustain the high sales growth rates of the early days. And ‘increasing at a decreasing rate’ isn’t something anyone wants to hear.

So have we landed a ‘whale’ yet? Nope, but we’re in advanced discussions with a few that we hope to come to agreements with soon. And it’s not just good for cash flow, it’s great for internal morale and to position Dasheroo for a better chance of providing long term value to our investors, and potential acquirers.

One note – take caution that one ‘whale’ doesn’t pull you out to sea with one-off feature demands that aren’t scalable to the majority of your user base! Happy fishing.

Track Our Startup: Dasheroo’s New CMO + Your Custom Data in a Dashboard

This past week has been another record-breaking week here at Dasheroo. We’ve been bringing our newbies from last week, up to speed and finalizing our monolithic billing project. Plus we worked on new hire on-boarding information.

Three More Newbies!

Dasheroo's new CMO and co-founder, Janine Popick.

Janine joins Dasheroo!

OK I’m very excited to announce that we brought on Janine Popick as our Chief Marketing Officer! You may know of Janine from VerticalResponse, the company she founded and ran for a whopping 14 years.  She grew VR from zero to over 1 million users, and pivoted to a freemium model before she sold the company to a big ‘ol public company a couple of years ago. She is also a contributor for and will tell our story there as well. As you can imagine, we’re pretty happy to have her. Disclosure time: I’m super lucky she’s also my wife 🙂

Read all about why she decided to come on in her newest article: 5 Reasons Why I’m Diving Into a New Startup.

Her first to do is improving our content strategy. Since we’re now officially launched, we decided to make this blog more product centric and talk to what we have to offer. From time to time we’ll also weave in how to use this amazing data we surface for you.

We’re attempting to have either of us write for outside publications. So perhaps this blog post might begin to appear on another site. This establishes us as experts at what we do (cuz people say we are!) and provides inbound links from quality sites. And that leads to improved search engine (SEO) results, so more people can find Dasheroo when they search for terms like ‘business dashboards’.

On top of this news, we’re also jazzed to announce that we’re bringing on the amazing Jenny Noyes who will be an awesome Customer Success Manager. She’ll  be looking at how users interact with Dasheroo and how we can make that experience the best possible. Jenny has a ton of experience working with small business owners for the last 8 years and knows the team well.

We’ve also got Derrick Reedy who is currently interning for the group working on getting us listed on a ton of quality sites as well as helping Mimi identify sales leads.

As a result of all of these hires (we’re up to 13 right now!) we’ve learned a bit about the importance of employee on-boarding

New SEO Strategy

We’ve taken a good hard look at our SEO strategy lately. We try to get noticed for the keywords “business dashboards” when someone searches on Google and now we’re going to take it to another level and try to get noticed for a myriad of keywords like social media dashboard and Google Sheets Dashboard.

We’re also looking to add a few more pages to the site and change-up our internal linking strategy as well. As many of you know SEO is a journey, not a destination. Video: Creating Custom Dasheroo dashboards with your internal data.

New Video

Alf put yet another amazing video together all about getting your internal custom data and shoving it into an insight on your Dasheroo business dashboards. Check this one out, we have 3 or 4 dashboards that take data from our database and we rely heavily on it to track progress.


We’ve been thinking of every which way a user may or may not pay us beyond our free (‘Tall’) version of Dasheroo, and we’re closer than ever. And to make a billing path seem simple is a ton of work, thanks to Josh, Andrew, Court and James for killing it! This Friday we’ll launch billing for any new person that comes to the site. As you know we’re business freemium so we always have a free plan for folks that don’t need too many bells and whistles but for those who do we’ll be charging a nominal starting fee of $19/month.

Cheers, John

Startup Lessons Learned: Hiring in Another State

OK, this may not be the sexiest post in the Startup Lessons Learned series, but it’s about one of those things that’s so easy to ignore, or in my case, not even think about when bringing on new team members in different U.S. States – registering your business to do business in that state!

I casually mentioned in a recent board meeting (remember that post about productive board meetings?) that we were building our presence in the lovely city of Austin, Texas and my lawyer’s ears perked up. “Are you registered in Texas?” Emma asked. And semi-confidently, I replied that yes, although we are based in San Francisco, the great folks at ZenPayroll had prompted me to fill out some various forms when I was adding my Austin-based folks to payroll (BTW, we love ZenPayroll, it’s super easy to use, very complete and just a very well done & affordable app.) So I thought I was all done. Not so fast, she said.

I also had to file a form to be ‘qualified’ to do business in the great state of Texas. It’s an Application for Registration of a For Profit Corporation (the TX Version). It’s an easy form to complete, and just asks for basic info like your business name & address, EIN #, names and addresses of company officers, and the address of the office (even if it’s a home office) in Texas. Oh yeah, plus $750 filing fee. And in about a week, Dasheroo was ‘legit’ to do business in Texas:

Signed, sealed & delivered - we're now legit to do business in Texas

Signed, sealed & delivered – we’re now legit to do business in Texas

We now have our first team member in Georgia. And now I know! Even though ZenPayroll does an awesome job of prompting me with any new payroll-oriented forms to complete, including Department of Revenue (need that payroll tax income!) and Department of Labor forms, there’s still that business registration form that needs to be filed with the Secretary of State.

So especially if you’re building a distributed team for your new business, remember to always check to see if you’re required to register your business in that state. I’m pretty sure every state requires it. It’s more of a housekeeping task than anything else, but take care of it at the get-go, right when you’re adding your next team member in a new state. Plus you’ll avoid potential fines down the road. Who needs that?

Startup Lessons Learned: The Importance of Employee On-boarding

Seems like we’re hiring like crazy lately! Suddenly every one of the co-founders of Dasheroo has at least one direct report. Wow. We are officially up to 13 awesome people – 10 cranking away now, 2 more signed and one ‘secret weapon’ we’ll announce soon!

We’re actually going to hold off on any more new hires, it’s kinda of like letting your food digest after you’ve had a big ‘ol meal. Plus, we need to start generating some $$ to offset our investment in our team.

OK, like I mentioned before we are a distributed work environment, with folks all over the SF Bay Area, Austin and a sprinkling of additional developers in Malaysia & Siberia. So the topic of onboarding our new people is something we feel especially strong about! It’s super key to communicate our story, our competitive benefits, our expectations, our tools and give a feel of our culture. This is even more important as we hire folks outside of our ‘family’, people we don’t have prior work experience with.

So what’d we do? We developed a couple cool Google docs, that’s what. One is called Onboarding Newbies and the other is simply, Dasheroo Glossary. We really have to work on some jazzier titles for these, but they are chock full of great info, all to get our next A-team Dasherooer up to speed in a flash.

(almost) all the basic info a newbie needs to get up and running fast & efficient at Dasheroo!

(almost) all the basic info a newbie needs to get up and running fast & efficient at Dasheroo!

The glossary includes not just our internal lingo, like ‘what’s an Insight?’ but also industry terminology, like defining what an API (Application Protocol Interface) is and why these are important to our business.

The on-boarding doc includes cool info like our story (why we started Dasheroo), information on each of our team, and our values.

We just shared these docs our Director of Sales, Mimi, who has been here for  3 weeks. She’s already provided info she wished she would have had on her day 1. Awesome!

We’ve also used Screenflow to create videos on how we do things, for instance like email marketing. A) It’s a great help to the new person who needs to learn how we do it and 2) they can refer back to it without continually asking questions.

Speaking of, I need to work on a Screenflow to record a demo to get folks comfy on how we position our product. That’s coming soon, as I’m sure lots of other helpful stuff as we get feedback from our newbies.

Now I wish we would have done this a couple months ago so all new folks could have had it, but hey it’s better to start it at Employee #10 than never!

What are your plans or policies for employee on-boarding? Let me know!

Startup Lessons Learned: How a Simple Question Can Pay Off

Hi. This is a great startup lessons learned this week. Several months ago, we started sending an email to new users 18 hours after they sign up. Gives ’em a little time to get into the app & kick the tires, but while they are still fresh.

It goes like this: the subject line is “A Quick Question” and the message is a simple text email from me:

A simple, 1 question email gets a 20%+ response rate and great feedback!

This simple email gets a 20%+ response rate and provides great feedback!

So this simple email gets a reply from more than 1/5th of the folks who sign up. As I mentioned a few weeks back, I can’t keep up with looking at all our new users like I could before we launched. So what are the benefits of this type of initial outreach? Here’s what I’ve learned:

  • First, the note seems to be appreciated (at least by 20%). I think that’s positive as it helps start forming more of a personal vs. company-only bond.
  • We get timely feedback where folks are finding us; that helps us with our marketing efforts.
  • Often our users will also share other great information – either a question, a feature suggestion or some candid criticism. It’s all good and we feed it right back to our product and support teams. We’re all about providing immediate gratification, so this rapid feedback loop helps us figure out if we are delivering on that promise.
  • And, here’s a ‘case in point’ example of how this simple question can start a dialog that builds the potential for bigger opportunities. Here’s a recent email discussion I had with Bill, who I later discovered runs a great SMB-focused agency. From Bill:
And the dialog begins

And the dialog begins

  • Great! Bill knows the competition, and allowed me to start a dialog. You don’t have to bother reading my reply below, I just provided him our competitive differences:
Here's my response to his question regarding how we compare to Cyfe

Here’s my response to his question regarding how we compare to Cyfe

I thought that might be the end of it, although I did plan to follow-up. But Bill was impressed that I took the time to answer him, which led him to jump in and set up some dashboards. That’s an important first step. And he continued wanting more info, this time about managing multiple clients within his account:

Now he feels more confident in Dasheroo, and wonders how to better manage his client accounts.

Now he feels more confident in Dasheroo, and wonders how to better manage his client accounts.

So surprise! We do have a type of user permissions called ‘Organizations’ which allows agencies to keep each client in a private silo. It’s somewhat hidden in the navigation, so I let him know where to find it, and he was jazzed:

Screen Shot 2015-06-21 at 10.54.14 AM

Bill then went on to ask me to connect on LinkedIn, and offered to open up his excellent network to me:

This dialog started with a simple question to a happy user to now, a referring customer!

This dialog started with a simple question, led to a happy user, and now a referring customer!

Excellent. We now have not just a happy user, but Bill plans on adding multiple clients and users into his account (which we love). Plus, now he’ll refer us, or help us get connected, to others in his network!

This back and forth probably took a grand total of 10 minutes. And that’s only because I’m a slow typer. So you may think you can’t take the time to respond back to each and every user. And maybe you don’t. But here’s what I’ve learned from this initiative – make it easy for users to begin a dialog and at the very least take the time to respond to people that seem genuinely interested. Sure you could ship it off to ‘support’, but as long as you can, answer these emails personally. It’ll keep your head in the game, fosters loyalty and can lead to some very valuable relationships!

Shout out to my bud and awesome marketer Ted Rubin, who created the concept of Return On Relationship; this is an excellent example of that in action.

Startup Lessons Learned: Productive Board Meetings

Hi there! Dang, how the weeks fly by don’t they? Hope yours is going great. Today we’re talking about the ‘dreaded’ board meeting. I only say dreaded because I’ve heard so many CEOs refer to them that way. But at Dasheroo? No way! (at least not yet;). So here’s some startup lessons we’ve learned to help you make the most of your board meetings – they can actually be enjoyable as well as hugely productive.

First, the frequency. When our lead investor and board member, Matt Holleran from Cloud Apps Capital Partners, mentioned that we’d be having monthly board meetings, I reacted with a “Soo…you mean as in ‘every 4 weeks’ monthly?”  Do you not trust me? What’s going on here?! No, it’s not a trust issue it’s all about collaborating, executing and working as a team to own the global business dashboards market. I genuinely love these frequent meetings; there’s no big surprises, the big issues are always top of mind, & we can nip other issues early on. At Dasheroo, I think we’ve developed a really productive groove with this frequency.

Now that that’s out of the way, something I was reminded of: board meetings aren’t sell jobs. Hell, that’s what you did when you were raising money! You need to be completely upfront on all levels and address f-ups head on. Sure, talk about the wins, but spend most of your time addressing misses, challenges and how your board members can help you out. That’s what they are there for.

Yeah, this is NOT our board meeting, please don't make it yours!

Yeah, this is NOT our board meeting, please don’t make it yours!

And similar to what I mentioned last week about building a valuable team, don’t bring on vanity board members. Make them count. Whether it’s deep industry knowledge or savvy business acumen to help grow your biz to the next level, judge carefully and choose wisely. And consider diversity. This should be a thorough interview process, not a free pass. The Center For Association Leadership has a good post about the various personalities you may encounter and how to deal with them.

Take notes. You need board minutes. So whether it’s someone from your legal team (we use Goodwin Proctor and love them) or your ‘Secretary’ (hate that word, but that’s how it’s referred to), or really anyone, make sure you do it. It’s required.

Last but definitely not least? Don’t make it a ‘bored’ meeting! Har dee har har. Sorry I couldn’t resist. Really, I am sorry. Anyhoo, who wrote the rule that everyone has to show up stressed and sit around some damn board table in a cramped room? “Oh look, they brought in sandwiches, San Pellegrino and Kettle chips!” Maybe you can tell I’ve attended my share of these. Loosen up the tie. For instance, think about your venue. So far, for our first 6 board meetings I have held them at a cool local restaurant called Sauce. They last 2-3 hours, we gather around my MacBook (although Sauce is happy to project it for me) and it’s a mix of more casual conversation and serious digging into the details of the biz. And always some laughs. As we grow? Who knows, will probably outgrow Sauce, but the spirit will continue on.

Remember, this is your board meeting, make it yours.

Startup Stories: How To Make Your Team Bigger Without Hiring

What am I talking about?! Here’s what I mean, and I think you all know what I’m getting at. Your ‘team’ is more than your co-workers. Sure they are the core, but without the support of others, you’ll never experience the level of success you can. Here are my startup stories this week.

So who are these ‘others’? Here’s my Key 3 that can add kick-ass value to your business:

Investors As Team

We are so lucky to have Matt and Judy from Cloud Apps Capital Partners, our lead investors in our Series A round, in our corner. If it was just ‘money’, I would have decided to do a small friends and family round and grind it out. Done that twice before, and was OK going down that path again. But when I started talking to Matt & Judy early on about Dasheroo, and the focus of their new fund (early stage + business freemium) I got intrigued. Plus, from what I already knew of their incredible connections, strategic focus and just overall ‘goodness’ I was sold. And from the get-go, their ability to help guide our strategy, establish our go-to-market plan and help establish partnerships blows me away.

Advisors As Team

It drives me bonkers when I see advisors as just names or business eye candy – good-sounding & looking names and faces to pretty up your website, but not folks that will help drive your biz. (Nothing personal but when Sheryl Crow went on the board of GotMarketing back in the day, I figured Got’s days might be numbered.) You need to really vet these folks out; they should be rabid about helping your cause. We currently have 3 top-notch, Grade-A rock star advisors. Who are they? I’m leaving that for an upcoming press release in the next week or so, but ‘who’ they are is not that pertinent for this post. They just really made sense for us from their ability to add value now, and over the long term.

One is a very successful and well-respected entrepreneur in the SMB world, and impresses the hells out of us with his practical, real world recommendations on what apps we should connect with or how we should price our agency offering. We have an all-hands with him each month. The second one is…well if I was a VC groupie he’d be on my list! He’s going to provide so much advice on how to successfully scale our business, and what pitfalls we can avoid along the way. And the third…that’s a real special one to me and our team for reasons that will be obvious when we release our press release. Tons of advice on scaling our young guppy to become a whale. She’s built a successful SMB from 0 to 1,000,000 users. Hell, that insight is gonna come in handy since we want every business in the world to have a Dasheroo dashboard!

Friends As Team

Either get them to help spread your word to their networks, plug them for some advice now and then, or both! For instance, my buddy Dave was a huge help in figuring out whether we need to charge sales tax or not; he’d just gone through a similar process with his own company. It saved me a ton of time, money and stress. Another ‘friend as team’ moment? My friend Kim included a mention of and link to Dasheroo in her company newsletter that goes out to 100,000+ SMBs! Free awareness and dozens of signups that day. So, Work Your Friends. But always give back!

What’s your experience working with advisors to expand your presence and grow your biz? Let me know!

Startup Tips – Lessons Learned This Week: Distributed Teams

Hi there! I hope you’re doing great, and that there’s some helpful startup tips in this week’s post.

This week, the biggest lesson I’m learning, will continue to learn, and hopefully get right (!) is building a distributed team. After 2 startups and mostly employing people in San Francisco, I don’t want to default into that way of thinking this time around. At least not yet. It’s tough here – rents are insane, competition for great talent is enormous, and…hate to say it but many folks here really seem ‘entitled’. I don’t need it. I’m not saying I won’t hire folks from the Bay Area, but it is definitely not a prerequisite nor does it give anyone an advantage when we consider who to bring on to our team.

First, why I decided to build a distributed team:

  • I’m not convinced people get more done jammed into one office. There’s a lot of distractions! I’ve experienced it many, many painful and expensive times.
  • Like I said, San Francisco is ridiculously expensive to hire and rent. I know, I live here!
  • Aside from the fact it’s SF, why not hire for ‘talent over zip code’?
  • Mature people appreciate the flexibility, and that should show in loyalty and productivity. Plus, I like working with (fun) mature people!
  • I am convinced you get the opportunity to build a more diverse group of people, and I like that. I think it breeds innovation.

Some things I am learning:

  • First – if you don’t keep up with Buffer, you need to. A big tip o’ the hat to co-founders Joel and Leo, they rock it. They are building a very successful, distributed team and are so transparent about how they do it. Lots of stuff to learn from these guys, thanks for the tips on your blog. If you’re ever in SF let me buy you several beers.
  • Like I said, bring on ‘talent over geography’. It also helps if your newbie has worked in an environment like this before. We recently talked to a great product marketing person, but after we talked a bit more, he really wanted the social aspects of working with other folks in an office.
  • If you are gonna do this, do it from the get-go. Retrofitting a more traditional office/HQ-based company to a distributed team would pose a significant challenge!
  • Just because there’s ‘no rent’ doesn’t mean there’s ‘no cost’ to supporting this structure. You may need more tools, more apps, more management time to make this work. And for sure you need to get everyone together periodically for some f2f time and fun. Is it quarterly? semi-annually? I’m not sure yet, but 3-4 times a year smells about right. That’s not free! But make it count, don’t cheap out.
  • And speaking of structure, even though it may seem less structured in many ways (working from home, easier to break off and take care of personal business, etc.) in fact a distributed environment does demand a ton of structure – trust, clear communications, great tools.

    Team Dasheroo at their offsite!

    Team Dasheroo all together!

  • Trust. Even more that ever. Transparency & trust. Do you feel it? Do they earn it?

We just had an all-hands meeting here in San Francisco. Hey, we’re 8 people. It’s pretty manageable, but it was really full of great energy, awesome ideas and bonding. We had it at my house, then ate great Mexican food at Don Pistos in North Beach.

Are you building a distributed team? Successes, hard lessons learned? Let me know!