Techstars Global Network Partner Pilot provides bookkeeping and tax prep services to startups so that they can focus on their business instead of their books. Techstars alumni companies can receive 20% off Pilot Core bookkeeping for six months and a free consultation call for setting up their back office.
By Waseem Daher, Cofounder and CEO of Pilot
My Pilot cofounders and I built and sold two companies before Pilot. In the process, we learned a lot about the pains and pleasures of building companies. At our first two companies, one of the biggest pains was bookkeeping, so our third business—Pilot—is all about solving that problem.
Along the way, we’ve become extremely familiar with the financial mistakes that startups make. Some of them Pilot can help you solve. As for the rest, here’s my best advice on what not to do.
The 4 Biggest — and Most Common — Mistakes Startups Make:
Mixing your company’s money with your personal money
Don’t do this. Seriously, just don’t. The official name for this is “commingling,” and it causes problems.
For one thing, if you commingle your company’s assets with your personal assets, you could lose the liability shield that you got by incorporating. This is what keeps your company debts separate from your personal ones. You don’t want to be on the hook personally for your company’s debts. Another problem with commingling: the possibility of owing lots more in taxes, if the IRS decides that stuff the company buys for you is actually compensation you aren’t paying taxes on. Not good.
My solution: Get and use corporate credit cards to make company purchases. This gives you a clean separation of work and personal expenses, plus you can easily see what the company is spending money on. If employees need to spend money on behalf of the company and then get reimbursed, use expense reporting software (I like Expensify) to do the tracking and reimbursing. Take a day early on in your startup and set this stuff up. You will not regret it — and if you don’t do this, I guarantee that you’ll spend way more than a day sorting out the mess later.
Want to get more expert financial advice for your startup, or hear more from Pilot founder Waseem Daher about how he built three successful companies? Register now for a live AMA (Ask Me Anything) with Waseem on February 20, 2020 at 1 pm ET. Register Now →
Not doing your taxes properly
This is a big one, so I’m going to break it down into the top errors I’ve seen:
Not filing corporate tax returns
You still have to file corporate tax returns, even if you made no money. Yes, there are penalties if you don’t do this.
Ignoring other fees and filings
You probably already know about state and federal tax returns and payroll filings. But there are other fees and filings you need to take care of as well. These vary by state and even city.
Missing tax credits
Your company might qualify for tax credits worth a lot of money. The R&D tax credit, for example, could save you up to $250,000 per year in payroll taxes if you qualify.
Not collecting W-9s as you go
When tax time rolls around, you’re going to need information about the vendors you paid that year. Don’t waste time begging already-paid vendors to go back and fill out paperwork in December. Have them fill out a W-9 at the start of the relationship, and you’re set.
My solution: Most of your tax problems can be solved by hiring a good tax preparer and keeping good records. Even if you feel confident in your ability to file your returns correctly and on time, consult a tax preparer to make sure you’re not missing any of those other fees and filings—or credits. Also, before you decide to do your taxes yourself, take a minute to run the math: estimate the cost, then compare that to your best guess at how much time it’ll take you to DIY your taxes, and factor in your level of certainty that you’ll get it right. Now go ahead and hire the tax preparer.
Most startups get into trouble with payroll because they don’t want to take the time — or spend the money — to set up a proper payroll system. But I guarantee that you’ll make a mess if you pay employees without a payroll system. You don’t want to be calculating tax withholding payments and form filings by hand.
Another hot tip: keep employee addresses up to date in your system. The wrong address can lead to incorrect state tax filings, and fixing these will be a major headache for you and your out-of-state employee.
My solution: Set up the payroll system. Yes, it’s another day that you’re setting up processes instead of building your business. Except that this stuff is building your business, and building it well. Techstars calls this slowing down to speed up, and I love that. If you want my recommendation for a payroll provider for your startup, I really like Gusto.
Messy financial records
Why do you need proper financial records? Three reasons: 1) filing taxes, 2) providing financial statements to a potential investor, landlord, business partner, etc., and 3) saving yourself time and money.
The first two are pretty clear. As for the third: you will spend way more time cleaning up messy records than you would have setting up good systems at the beginning. Plus, good clean records mean that you won’t make mistakes like paying double charges, which can add up fast on large items like rent.
My solution: Hire some help. For our first startup, we did the books ourselves, and in retrospect it was a mistake. I didn’t think it would be a huge burden, and I thought it would keep me closer to the details of the business. I was wrong. It took a surprising amount of time to do well, plus my time was better spent focusing on running my business. Even financial professionals hire bookkeeping firms to take care of their day-to-day stuff.
Ultimately, most of this advice can be summed up as keeping your personal and company money separate, keeping good records, and hiring experts for your taxes, payroll, and bookkeeping. The first two are plain good sense. As for hiring those experts, I have seen over and over how much time and money startups waste trying to do these things for themselves — usually in an effort to save time and money. Learn from their mistakes.
Waseem has lots more financial advice to offer startups — and he’d love to take your questions. Register for a live AMA (Ask Me Anything) with Waseem on February 20, 2020 at 1 pm ET. Register Now →
I haven’t always been a big reader, but I’ve got more into it over the past few years of working with startups. In a past article, Five Pillars of Success: Curated Content for Early-Stage Entrepreneurs, I mentioned that last year I read 12 books. This year, instead of aiming for double (24), I set myself a stretch goal, and I’m aiming for 48. Will I make it? I’m going strong so far.
With all this reading, I’ve come across some great books. I know lists are supposed to be top 10, but I loved all 11 of these too much to cut one off the list.
Here my 11 top reads for early-stage entrepreneurs:
11. Start With Why: How Great Leaders Inspire Everyone To Take Action, by Simon Sinek
Why are you building this company? Why should people listen? Why are others successful, and you aren’t? This book may make you rethink why you’re building what your startup—but it will also surely help you tell your story better… or get you to work on something more aligned with your why.
10. The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, by Eric Ries
A book for aspiring entrepreneurs and early stage founders, Ries breaks it down into simple steps: how to systematically approach building your business, get it validated, make it profitable, and set up the basics for it to grow.
9. Do More Faster: Techstars Lessons to Accelerate Your Startup, by David Cohen & Brad Feld
Written by our Techstars co-founders, this book is an easy read of bite-sized advice from across the brilliant worldwide network itself. Perfect for those who are new to the startup world to and want to figure out how to set up your company, get customers, hire—and many other must-knows for any early stage entrepreneur.
8. Delivering Happiness: The Path to Passion, Profits, and Purpose, by Tony Hsieh
If you’re building a company and want to learn about how to make a good customer-centric business, with the best company culture, this book will show you how. It’s about more than just business, though, it’s also about life.
7. Lean In: Women, Work, and the Will to Lead, by Sheryl Sandberg
Every company should make this book mandatory reading. It opened my eyes to gender inequality. While putting some responsibility on men to support women more, it also details how women can take the lead themselves to take part, aim higher, and take more risks.
6. Sprint: How To Solve Big Problems and Test New Ideas in Just Five Days, by Jake Knapp
Know what the biggest startup killer is? Lack of market: when you build something no one wants. This is the book that the Google team wrote and practiced, and it will show you how to test (and possibly invalidate) ideas in five days. My team at Evolve used it before we sold our company to Hubspot, so I can tell you that it really works.
5. Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets, by Al Ramadam, Dave Peterson, Christopher Lockhead, and Kevin Maney
This book explains how launching a startup is more than about creating and launching products. It discusses why you should consider launching a product category, and how and why to condition the market so they demand your solution.
4. Hacking Growth: How Today’s Fastest-Growing Companies Drive Breakout Success, by Sean Ellis & Morgan Brown
In my opinion, the number one growth marketing book of all time. I’ve read it yearly since 2010, and recommended it to every founder I meet. Need customers? Is your current customer acquisition strategy not working? Not sure how to run marketing experiments? Read this!
3. Never Split the Difference: Negotiating as if Your Life Depended On It, by Chris Voss
Written by an ex-FBI hostage negotiator, this is the book that every one of my book club members said I have to include here. It’s the way to get better at negotiations and influence—and get what you want. Note: it’s not just useful for sales people, it’s helpful for all types of negotiations, or even discussions with partners, friends, or family.
2. Mastering the VC Game: A Venture Capital Insider Reveals How to Get from Start-up to IPO on Your Terms, by Jeffrey Bussgang
This is one you won’t find on other lists. It’s a perspective from the other side: an entrepreneur turned VC. So keep this a secret. Knowing how they think will help you plan your moves. It’s a little more technical and financial than the others here, but it’s worth the read when you’re a little later on and want that opposite perspective.
And my #1 recommendation is….
1. Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future, by Ashlee Vance
If you’re looking for inspiration about changing the world, look no further. In my eyes, Elon is by far the greatest innovator of our time. I mean, he brought together a brilliant team, and learnt how to build a rocket from scratch, for a lot less money too. I also really appreciate that Elon didn’t get “final revisions,” so the book has a certain raw, unbiased lens.
So now what? Go read the books. You don’t have to read one a week like me or even one a month, but if there’s one thing I learnt from all of these books, you have to set goals so you can stay motivated and keep it consistent.
Lastly, don’t forget to reread your books. In case you didn’t know, the most successful people in the world all say that you shouldn’t just read a book once and put it away. The best part is reading it again when older, smarter, at a different stage, or after you’ve gone through different experiences that the book touched on — unlocking more value from the book for you.
What are some of your favorite book recommendations? Tweet me @iamsabakarim
How to be a Considerate Communicator
By Ray Newal, Managing Director of Techstars Bangalore Accelerator
The Metaphor of the Traffic Light
On a recent bike ride, while passing through a four-way intersection, a thought occurred to me regarding the role of contracts and signaling systems in interdependent situations. Without traffic lights, speed limits, and a contract between drivers to obey the traffic laws, cars would crash into each other a lot more than they do. Bike riders like myself would never stand a chance. The combination of signaling systems and contracts allow us to bring order to chaos. In the case of traffic, these systems help us get from point A to point B in one piece.
But what happens when the signals and associated contracts are no longer relevant to our behaviors, or can’t keep pace with the magnitude of interdependencies? Technology has a way of impacting human behaviors and sometimes making them obsolete. When behaviors change, we need new ways to manage them. Prior to traffic signals, cars and carriages were sufficiently sparse and slow enough to allow the driver (or rider) to visually assess the situation at an intersection and act accordingly. As cars became cheaper and faster, and roads became more highly trafficked, the visual approach stopped working, leading to the advent of traffic signals and road signs.
While communications started out as a simple interdependency, it too has become increasingly complex.
The Telephone and the Mailbox
Here’s a previous, universally accepted communications contract: the sender would dial or write when they had something to say, and the recipient would pick up or respond when they recognized an incoming call or a letter in the mail. This contract and signalling system worked very well when communications required us to be physically proximate to the telephone or letterbox in order to receive calls or letters. It worked because the expectations of the caller or sender were defined by the chance that the receiver would be by their phone, or in the case of letters, that the mail would probably arrive—at some point. It was manageable and even fun for the recipient to get phone calls after dinner, or check the letterbox on the way home from work. On the off chance that the phone rang, or a letter was discovered in the letterbox, these communications received the full attention of the recipient—even a telemarketing call may have been received with pleasure!
Our Relentless, Wireless World
In a wireless world with devices always readily available in our pockets or purses, we find ourselves in dire need a of a better contract and signalling system. Even though our devices never leave our sides, the device in your pocket now works harder for the sender, making sure those competing calls and messages get heard as soon as they arrive. Instead of making life easier, mobile and internet communication has conspired to create a feeling of obligation on the recipient side. The result? We feel like we have to be perpetually responsive to communications, regardless of whether we are focused at work, exercising at the gym, or spending quality time with loved ones.
Wireless technology, communications software, and mobile telephony have gradually increased the volume and frequency of communications, making us ubiquitously accessible, and creating a perceived obligation of round-the-clock responsiveness because we have yet to develop any new contracts or systems to deal with this increasingly complex interdependency. Just as there are potentially fatal consequences of traffic flowing without mutual acceptance of traffic signals and rules, there are also significant consequences of communications traffic flowing without a system that respects our ability to receive those communications with mental availability, and attention.
With the traffic light stuck on green, the flow of communications never stops, and our lack of attention has become the unfortunate by-product. In work and life, events that receive our full and undivided attention are rare and infrequent. Indeed we’ve stopped being present for much outside of what happens on the device in our pocket.
A New Contract for Communication
In the absence of any better signalling system for our digital communication, we need to develop a new contract for communication that is less reliant on the recipient to manage their accessibility. Considerate communication requires us to be conscious and empathetic of the recipient’s attention by selecting how and when we communicate with them. By considering the recipient, we also optimize the receptive value of what is being communicated, meaning we get the responses we need when we need them.
Here are some of my ideas on things we can do to be Considerate Communicators. I’d love to hear your ideas in the comments!
Skip the cc
Let’s all agree to avoid copying each other on emails. I get it, copying is to ensure everyone relevant to a given subject is in the loop. Slack is a better tool for this: it’s a great repository for FYI’s, group discussions, and media pertinent to a topic. Instead of using email to keep everyone in the loop, let’s use email to send things to people who need to receive and respond to that specific subject.
Set email priorities
In email, there are things I need to respond to ASAP, and there are things I need to look at within the next day or two. For anything else, we shouldn’t be using email. Let’s use the tools that come in just about every email system these days to mark priorities, so that no one misses a message that needs to be seen and responded to within the next day. Everything else will get a response within 48 hours. If it doesn’t require a response it won’t be sent as an email, it will go to Slack.
When something needs to be seen and acted on NOW, there are tons of tools that do a good job of grabbing someone’s attention. At Techstars, we use Voxer for truly urgent communications. You could also use messengers like Whatsapp, Facebook, Telegram, Slack DM, etc.—whatever works for your company, as long as you set expectations around that particular platform. Let’s use these sparingly, because very rarely does anything actually need to be responded to right away. Let’s not use calls unless it’s an absolute emergency. Unscheduled calls should fall within the domain of one’s friends and family members.
Let’s move complex multi-angled discussions to the place that complexity is best managed: scheduled synchronous communication. This can be Skype, Hangouts, phone calls, or a good old coffee meeting. Whether these are one-on-one or involve a group, these discussions are always best handled in real-time. But even if it only requires a one-on-one conversation, let’s remember to respect each other’s time by scheduling the conversation. An IM chat can also become an easy entry point into a synchronous voice or video discussion, if both parties agree to it.
Respect the time block
Let’s honor and respect each other’s time blocks. Short of having a tool to manage our mutual awareness of each other’s time blocks, let’s just agree to not send work communication outside of the workday that requires an immediate response, unless it’s an urgent/crisis situation. Every workplace has its own definition of what this means, so feel free to interpret the word ‘urgent’ in a way that suits your environment. If you’re working across time zones, respect the clever default DND in slack, or build this into your expected response times for email and other modes of communication.
Let’s use Slack (non-DM and general channels) as a way to inform everyone. This means we have to stop using these channels as if they were continuous Whatsapp conversations, and instead add context to discussions so that those coming in later (that day, week, or year) can make sense of what is being shared.
A World With More Intentional, Better Communications
If we start becoming more intentional about being considerate communicators within our teams and with our friends and family, we will start to see some of the principles spread externally. It won’t happen immediately, but eventually our inboxes will be lighter, our Slack channels will be richer with context and information, coming back from vacation won’t be so daunting, and quite possibly, we’ll look forward to answering our phones again.
How do you keep your inbox lean and your startup team in sync? Share your favorite tips and tricks in the comments!
By Shannon Liston, Techstars Corporate Council
Just to be clear: This sheet is for informational purposes only and does not constitute legal advice or create an attorney-client relationship. Companies should consult their own attorneys for legal advice on these issues. Because of the generality of the issues discussed in this piece, the information provided may not apply in all situations and should not be acted upon without specific legal advice based on particular situations.
Sometimes, startups fail.
It’s painful and brutal—and nothing to be ashamed of. It’s part of many, many entrepreneurial journeys. But along with the emotional ups and downs, you’ve got to deal with the practical legal side of shutting down your startup.
The legal name for one version of this is corporate dissolution. If you don’t need the protections of bankruptcy (you’ve got low risk of litigation or disputes over claims), corporate dissolution may be right for your startup.
The Techstars legal team has created this best practices sheet to give you guidance and practical tips if your company is facing dissolution. Unsurprisingly, these will be different depending on which state you’re incorporated in—this sheet focuses on Delaware, because of the large number of US corporations incorporated there.
Long-Form v. Short-Form Dissolution
Many smaller companies liquidate without the protections of federal bankruptcy law, as corporate bankruptcy can be very expensive. Instead, you can get some of the same protections through Delaware’s long-form dissolution process—it gives boards of directors similar protections, and provides company creditors with notice, plus an opportunity to present their claims.
Work with your legal counsel to make sure you meet all the formalities of the long-form process, like 60-days notice to all known claimants, including public notice, and a court approval process ( 8 Del. C. 1953, § 280).
The formalities of the long-form process may be overkill for your company, especially if you’ve already sold your operating assets, if you stopped operations a while ago, or if you’re unlikely to have unknown creditors.
In this case, short-form dissolution may be right for you: it’s simpler and less expensive for many companies, and comes with fewer formalities than the long-form process (8 Del. C. 1953, § 275).
7 Steps to Dissolve a Business
- Obtain Board and Shareholder Approvals. Your company’s Board of Directors must approve the decision to dissolve and adopt a Plan of Liquidation. A majority of the company’s shareholders must also approve the decision and the Plan of Liquidation.
- Pay Franchise Taxes and File an Annual Report. You must pay Delaware franchise taxes in full (including the current calendar year franchise tax) and file all applicable Annual Franchise Tax Reports. The Delaware Division of Corporations will not accept the Certificate of Dissolution (see below) until this step is done.
- Notify the IRS. Within 30 days of the Board approving the dissolution (the dissolution resolution date), your company must file a notice of dissolution with the Internal Revenue Service: Form 966.
- If the dissolution involves the sale or exchange of corporate assets, Forms 8594 and 4797 might also be necessary.
- See the IRS checklist for other required filings.
- File for Dissolution with the State. Once the decision to dissolve is properly approved, the company must file a Certificate of Dissolution with the Delaware Division of Corporations.
- If your company has stopped doing business and doesn’t have any remaining assets, it might qualify to file the short form certificate of dissolution.
- If the company is registered to do business in another state, it will have to withdraw or surrender those qualifications.
- Provide Appropriate Notice to Creditors and Stakeholders. Follow state law requirements to give notice of the dissolution to anyone with a claim against the company. Delaware’s long-form dissolution notice requirements are here: 8 Del. C. 1953, § 280.
- “Winding Up”. After the dissolution is effective, the dissolved company is deemed to continue, generally for three years, for the limited purposes of winding up per the Plan of Liquidation. This means:
- Settling and closing the business;
- Liquidating remaining corporate assets;
- Settling claims;
- Resolving any lawsuits;
- Making final distributions to creditors, and if funds remain, to applicable shareholders.
- File Final Federal and State Tax Returns. Review the IRS checklist for closing a business and filing final returns. For the company’s final returns, check the box to indicate the tax return is a final return.
Do’s and Don’ts
Do: Act in accordance with your fiduciary duties.
It’s your responsibility to focus on maximizing the company’s value. For more on your obligations as a Director, see here.
Don’t: Disappear; act in a manner that presents a conflicting interest; arbitrarily pay back one creditor over another; etc.
Do: Send the filed Certificate of Dissolution to investors, describing your decision to dissolve and your efforts to maximize return to shareholders.
Don’t: Use dissolution as an escape hatch.
Dissolution alone does not abate actions, suits, or proceedings begun by or against your corporation prior to dissolution—or, generally speaking, for a period of three years after dissolution.
Do: Educate yourself on the several ways to wind down a company.
Talk with your lawyer about which way to wind down your company is the best choice for your situation—the complexity of your company (number of employees, investors, creditors, etc.) will have a big impact on this.
By Sabrina Kelly, Techstars Vice President of People Operations
At Techstars, we define our mission in People Ops as the following: “We are strategic partners in building Techstars business by maximizing the value of our most important asset—our people. We attract, retain, develop, and support Techstars employees globally and aim to uphold our culture and values, in a manner that is inclusive to all.”
As VP of People Ops, I hear a lot of questions from founders. This series aims to answer the most frequent questions.
Q: What is the single biggest People Ops mistake you see startups make?
Hiring the wrong leaders and not course correcting soon enough.
Hiring leadership is hard at any stage, but there is a crazy amount of pressure on startup founders to hire them quickly. It’s really easy for founders to lose sight of the values that are important to them in these hires, due to pressure from the Board or other advisors on “who” and “what” is right for their business. This whiplash is amplified by the fact that they likely have a bunch of employees that need experienced leadership, and they are band-aiding that at the moment themselves.
Mainly, don’t ever make that hire unless you are 110% pumped to sit in the trenches with them.
My advice, as impossible as it might sound, is to take the time to get it right: be extremely thoughtful about the profile you are looking for, get alignment with your leadership team on how to interview, proactively source from diverse pipelines or hire a recommended agency to support. Mainly, don’t ever make that hire unless you are 110% pumped to sit in the trenches with them.
So, what if you do all of that and in six months you start to sense that it’s not working? As painful as it might be, you need to dedicate the time to figure out what the problem is—and if you find out it’s them, you let that person go as soon as humanly possible. It might feel like the company will crumble if you have to start over, but that pain is nothing in comparison to what can happen if you put up with the wrong leader for too long.
Want to #DoMoreFaster? Apply to a Techstars mentorship-driven accelerator today.
Techstars Mentor Jason Mendelson recently gave a talk to the Boulder program called, “20 Ways to Blow Up Your Company.”
Here are a few highlights. Be sure to check out all the details in the video below!
- Pick a Bad Idea
- Pick Bad Employees
- Being Arrogant
- Focusing Only on What You Don’t Know
- Being Overly Emotional and Not Analytic
- Know Your Business Model
We recently held an AMA with Techstars’ Co-CEO, David Cohen, where he answered commonly asked questions from founders about topics such as forming a team, developing an MVP, and applying to an accelerator program.
Any advice to founders who need more resources to develop an MVP or a presentable prototype? What’s the best method of getting investors to hear out the idea/plan when you don’t know anyone in the community?
These are kind of different questions so I am going to go at them separately. I’ll tell you a quick story of a company called Everlater that sold to MapQuest, AOL and came through Techstars. When I first met Nate and Natty, they were Wall Street types and loved to travel. We funded them, but we only funded them after watching them try to learn how to program.
They were so passionate about this idea coming out of their minds into the world that they actually taught themselves how to code – they were terrible at it, not very good at all. But later on, they got better, but it was still a crappy prototype and a crappy MVP. So step one is, having something is better than nothing.
If you can’t find somebody to do it, my question is, why can’t you do it? Do you think that writing a little software code is something that you have no ability to learn? It tells me something about you, that you are not willing to try. You could find a friend who does know how to program to spend a couple hours with you and show you how to get going.
You could say look, this is what I am talking about, it doesn’t work yet, but it’s what I’m talking about.
I believe great entrepreneurs do stuff.
If you can’t do that and you are allergic to keyboards and computers and you’re just never going to code, that’s cool too. Some of these languages, by the way, are very easy to learn now, it’s not like learning a foreign language, you can get a lot of help from the editor, and there are various simple languages out there that you can learn how to prototype things quickly.
There are lots of coding classes available online, so my first question is, why aren’t you doing that? If you can’t get somebody in the world who has those skills excited enough about what you are doing, or you can’t make friends with somebody who can help you with that, that is also a red flag for me as an investor.
The answer to the question is like anything else, just do it. That’s why it is Nike’s slogan, it’s so great and really the easy answer to a lot of things. Plus, I’m an early stage investor, I don’t care if the prototype is presentable, it doesn’t have to blow me away. You just have to start the meeting and say look, I hacked this together myself, we need funding to hire engineers and obviously the user experience is terrible. You know it is terrible, but that’s okay. You’re self-aware, it doesn’t have to be beautiful and great.
I think doing attracts investors. Talking about doing makes me think maybe you’re not an entrepreneur.
For the second part of the question, I would take a quality over quantity approach. I would find someone who does know the investors that you are targeting and I would figure out how to spend time with them. For example, I would go to someone that they funded or someone that they have worked with and mentored before and say, will you help me with this? They are likely more available than the investor and I would use them as a way to create an introduction to the investor.
I would also suggest you read my blog post on DavidGCohen.com called Small Asks First. It’s about the idea of not over-asking, which is really important in entrepreneurship. You are trying to get to a resource, it is very busy, so get an introduction from somebody they know – it’s not that hard, and just ask them for something small.
Let me give you an example of something big – lunch. Lunch is very big – you’re asking them to go spend time with somebody they don’t know for an hour, which is an awkward situation, especially if they’re an introvert like I am. That’s a big ask. I know it feels small to you but it’s a really big ask to me. Coffee – huge ask. I have another blog post called Coffee or Lunch? that I wrote on this topic. They would have to go out of the office, meet you somewhere, and the biggest thing is, I don’t know you… it’s a big ask for a first ask.
Here’s a small ask – send me a paragraph or two of why I can be helpful to you, and the one really simple thing I can do to be helpful to you. I have another blog post that is called The Perfect Email. Somebody wrote me out of the blue, not even introduced, with enough context that I thought it was the best email I ever read and so I reacted to it. I ended up having an exchange of dialogue with that person; I even blogged about it. I don’t know what happened there, probably nothing huge, but hopefully I was helpful in some way.
I think the context of why you’re reaching out to me and asking for something that is easy for me to do is great, because going to have lunch is actually not easy to do – I’m busy, I’m introverted, etc. What is easy is asking me to click on a link and tell you what I think of the messaging on your website, the primary tag line or whatever. If I don’t respond to that, I’m just an ass. That takes ten seconds for me to do. It’s a small ask, it creates engagement, I can just click on the link, see what you’re doing, have to think about it for a second and then respond. Now, you’re actually starting a dialogue by making a small ask of something that is very easy for that investor to do. That is a great way to build a relationship and you go from there. You can do that at scale to figure out who is interested and engage more with those people.
Eventually, you’ll end up having lunch and a meeting.
At Techstars, we fully believe in the idea that no one is “too far along” for Techstars. Inversely, nothing is too early. Techstars has a program for every step of the entrepreneurial journey – from startup programs like Startup Digest, Startup Week, Startup Weekend and Startup Next to later stage offerings, including the accelerator program and venture capital for add-on funding.
Today’s post comes from Nishika de Rosairo, CEO, Creative Director, and founder of dE ROSAIRO. Before becoming an entrepreneur, Nishika built a corporate career with Deloitte, Cisco, and Salesforce. In addition to leading her business, Nishika serves on several boards including Startup Women, Upward, and the Center for International Business Education and Research.
“Aren’t you scared?”
“What will you do if you fail?”
“You have no experience in the industry, how will you succeed?”
“Don’t worry, you can always go back to Corporate America”
… and so the questions and comments flooded in…
What surprised me the most was that these questions and comments were being dished out from a combination of people who knew me very well, and also from those who didn’t know me at all.
I soon started to realize that non-entrepreneurs were projecting their own anxieties of starting a business onto me.
So the real question became:
How do you listen to the parts that matter, and turn off the parts that don’t?
An Entrepreneur is Born
For me, entrepreneurship has always felt very real. I was still a teenager when I came to the realization that life would be boring if everyone succumbed to practices and principles denoting linear patterns of thinking and execution, simply because they made life easy to explain and easy to understand.
My version of happiness started to emerge around the same time when I turned to mentors such as Sir Richard Branson and Anthony Robbins. They taught me that happiness was a state of mind, achieved through a non-linear journey of strategy, discovery, and perspective: the perfect mindset for an entrepreneur.
I grew up with an adventurous spirit, and by the time I reached my 30s, I was living on my fourth continent, had traveled to over 40 countries, and my career in the corporate world was ripe and flourishing. Over my 10 years in Corporate America, I had the incredible opportunity of learning a repertoire of deep knowledge and expertise from the best of the best: Deloitte Consulting, Salesforce, Apple, Levi, Cisco, Chevron, and many others.
Even still, I wanted more.
I decided it was time to turn in the stability of a steady paycheck for something that was much more adventurous and impactful.
I wanted to change the world, one design at a time.
Building a Business
Finally, my business – dE ROSAIRO (pronounced ‘day ro-zai-ro’) — was born: it was a childhood dream coupled with a deep desire to influence the world through the inherent psychology behind the clothes we wear.
I spent 10 months writing my business plan and building the business on nights and weekends, all while still employed full time at Salesforce. At the end of that time, I had my first collection of sketches sitting on hangers in a sales showroom in Los Angeles. I built dE ROSAIRO on the founding principle of ‘Look Feel Lead’, which translates into — how you Look, is how you Feel, is how you Lead. The idea being that how we dress influences how we feel, and on the flipside, how we feel influences how we dress.
No matter how many people have shared their years of wisdom with me, not one person, or any one experience, could have truly prepared me for the broad depth and range of mental and physical strength it takes to be an entrepreneur.
Doubt is Part of the Journey
There are days I have wanted to pull my hair out, and then there are days that I know I am doing exactly what I should be. I would be lying if I didn’t admit the rough days.
But the truth is: doubt is a part of the journey, as it continues to provide me with an opportunity to question even my most basic set of assumptions. Healthy businesses cannot be built on complacency and self-assurance.
Mistakes will be made, money will be lost, and through it all, the question that we will need to keep answering is – am I still aligned with my vision?
Why does alignment matter? It matters for two key reasons:
- When we launch a business, we should aim to build a foundation that aligns with our personal set of values. We need to ask ourselves: what matters to me? How do I want to affect the lives of others? What do I want my legacy to be?
- Doing ‘good business’ is no longer the icing on the cake; in today’s world it is a basic expectation. This means we each have a role to play.
Through this journey, what I’ve come to discover is: there is no greater measure of self-fulfillment than when profit, individual values, and ‘good business’ intersect.
So when you’re on the brink of YOUR entrepreneurial journey, and when people ask you:
“Aren’t you scared?”
“What will you do if you fail?”
“You have no experience in the industry, how will you succeed?”
Tell them that you would rather give it your best shot than regret not trying.
Tell them that you desire transformative growth in your life that a steady paycheck cannot provide.
Tell them that changing the world is worth the calculated gamble.
Sara Capra is the co-founder of Orate – a DC-based startup that makes it simple for event organizers to find speakers within their budgets.
Orate’s story began last year at Startup Weekend DC – an event where participants launch startups in less than 54 hours. Orate took first place in that weekend’s competition – even though Capra had taken a chance to be there in the first place.
Capra entered Startup Weekend with some concerns that her idea wouldn’t resonate with event participants. She was quickly proved wrong — she and Orate co-founder Veronica Eklund ended up building the largest team, which developed a mock-up of the future platform.
Sara shared Orate’s journey with Startup Weekend DC’s Elvina Kamalova. Answers have been edited for length and clarity:
Tell us about Orate.
Orate is an online platform that simplifies the process of finding, vetting, and booking public speakers simple. Our mission is twofold: 1) Make it easy to find quality speakers on any budget; and 2) Assist speakers in more effectively marketing themselves and getting them in front of the right audiences.
What was the role of Startup Weekend in starting and developing your project?
The Orate journey began at Startup Weekend DC in 2014. It was the launch pad for what Orate has become, and sparked the initial evolution of the concept. We began with an idea to alleviate the stress of filling last minute speaking cancellations. That resonated with many people, but through the feedback process over the weekend, we decided the business model around that was not one that would be sustainable.
Through our mentors, sending out surveys, and in-depth conversations with the team, we decided the business model needed to be based on more than that. Startup Weekend helped to give us the ecosystem and structure we needed to take our first big step in understanding how to test and validate our ideas.
How did you build your team?
Building the team during startup weekend was mostly organic. Initially, I was concerned there wouldn’t be enough interest. One of the great things about Startup Weekend is that you only need two people to work on an idea. My co-founder attended and joined my team, so we would be able to explore the idea no matter what. It turns out there was quite a bit of interest, and we ended up with the largest team in the competition. I thought our most important team member would be a developer, ideally one who knew front and back end since this was meant to be a web and mobile app.
One of the most important lessons I learned that weekend was how much you can do with a little bit of resourcefulness and creativity, when there’s a lack of technical expertise. We had a wonderful graphic designer.
As opposed to trying to build out any applications over the weekend, she instead mocked up what we wanted the website to look like. That way, we could walk the audience through the customer journey, without getting too bogged down with feature aspirations and technical details. After all, it was just the beginning! We knew if so much could change in one weekend, there were many more changes to come.
What are the biggest challenges in your startup journey?
The biggest challenges have shifted over time. Initially it was staying focused. There were so many things to be excited about – potential partnerships, big ideas, ideas within those ideas, the way you envision the company 1, 2, 3 years down the road.
The challenge is taking that long-term vision and working backward to map out your trajectory starting with today, and breaking down steps for initial short-term growth. We’re over a year in and have now seen a lot of our early ideas come to fruition. We are still constantly brainstorming, but we’re much more skilled at capturing ideas for a future state, and continuing to stay focused on the short-term execution to make them happen.
The other challenge we face is getting into the heads of our customers. Collectively, we’ve conducted hundreds of formal and informal interviews, feedback surveys, and tests. While there are times that what users say and what they do are parallel, we have found that monitoring their actions is most effective.
Did you have technical skills coming to SW?
Aside from some basic HTML (we all had MySpace, right?), I didn’t have any experience with coding going into Startup Weekend DC. However, attending the event and launching the company inspired me to spend more time learning about software development, and gave me the ability to discuss the basics of other languages when I need to.
Tell us how you realized your goal for building your venture.
I’m still getting there! We are in the middle of fundraising to get to our next phase. We have achieved a lot so far. We’ve scaled our speaker database extensively, had only positive feedback from clients, and launched a new website and subscription service. While I’m proud of what we’ve accomplished, we don’t rest on our laurels. We have big plans moving forward and the wonderful team me and my co-founder have built is at the core of making those happen.
How did you raise your first funding?
We socialized Orate early and often. We pitched a lot, organized the data and financial information we had to help us have informed conversations, and put all of our cards and chips on the table. Our initial round was mostly from angel investors, and some funding came from the accelerator program Orate participated in called The Startup Factory.
What would be your advice to starting entrepreneurs?
Sharpen your communication skills. Entrepreneurs must always be networking and selling, even if their title or job responsibilities don’t formally include it. Entrepreneurs have to effectively communicate with and motivate their team to execute on the vision. They need to be good role models, and inspire the team to be brand advocates. Establishing and growing relationships are crucial to starting a company. Being a genuine, impactful, and effective communicator, is instrumental in that process.
It’s also important to get comfortable being uncomfortable. Take the “no’s,” the risk, the ambiguity, self-doubt, and constant change, and learn from it all. After you learn from it, embrace it. Two of the best things about life are that almost nothing is final and the possibilities are endless. Reflect on the lessons you learned, what led you there, and use them to make better, more informed decisions moving forward. This is one of the reasons it’s crucial to have good advisors and mentors. You need a brain trust that can help you step back, put things in perspective, and work through challenges.
To start your own startup story, join us for Startup Weekend on September 25-27. Register here and buy your tickets today!
With an acceptance rate of a dismal 1 percent, getting into 500 Startups’ accelerator program is definitely not easy. To put that number into perspective, Stanford’s fall 2012 acceptance rate is a more encouraging 6.6 percent.
Now, to work on a bitcoin startup and get accepted into the prestigious accelerator program, that is even more challenging.
So how did CoinPip, a bitcoin wallet service and payment solution for merchants in Asia started in January 2014, get accepted into 500 Startups Batch 11?
Back in 2010, the seeds of CoinPip were already planted when Ben Bernanke announced Quantitative Easing (QE) infinity. Anson Zeall, now founder of CoinPip, was then a successful hedge fund manager returning 35% P.A. for investors. He thought it was time for something else when he heard the news. A friend of his then introduced him to bitcoin and he jumped in.
Within a short span of 1 year, the company has expanded operations quickly into neighbouring countries – Indonesia, Taiwan, Hong Kong, Singapore, Philippines and even the USA. However, not all was easy and smooth sailing. In mid 2014, the company was running out of money. Around this time, a group of startups in Singapore, together with CoinPip, started the Association of Cryptocurrency Enterprises and Startups Singapore (ACCESS). This caught the attention of Sean Percival – venture partner at 500 Startups and the road to securing their seed funding began.
The first secret is – Do something big and bold to show your belief
This coming Friday, 17th July, Anson Zeall will be sharing with participants of Startup Weekend Asia-America in person, his personal story of overcoming all obstacles to finally building a company in the Bitcoin space that spans across countries in Asia and America.
See you there!
Startup Weekend Asia-America
July 17th-19th, 2015