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Bootstrapping a Business:  

Tips from Startup Experts or Successful


Founders for Bootstrapping a Business
Pere Hospital
Pere Hospital
The Co-founder & CSO of Cloudways said:

• It is a marathon, not a sprint!: Don’t rush, don’t try


to overachieve, don’t burn yourself out …
bootstrapping a startup is like slow food: find the
right healthy ingredients. mix them with craft and
be patient to get an outstanding result. Time is in
your favor. A funded startup needs to rush to grow
to be able to get to the next raise in shape to repeat
the cycle again … time is against them.
Pere Hospital
• A fool and its equity are soon parted: Again
patience. As you bootstrap your business and grow it
nicely, opportunities will pop up to get funding, sell
… Think carefully and time it properly and don’t take
the money if you don’t know what you will do with
it. A typical and very reasonable option would be
liquidity for the founders. Build relations to make it
happen when and how you want it happening.
Pere Hospital
• Be unforgiving when hiring: In hindsight, I think
this is key. Of course for every kind of company, but
bootstrapped startups have a very short runway.
Mess it a couple of times or in certain positions and
you are mostly done. Research on best hiring
practices, don’t take shortcuts, don’t settle for
“good enough”.You need outstanding people with
complete culture fit and vision alignment to get
where you want. Take this as your main job
(among a zillion others) as a founder.
Jake Nickell
Jake Nickell
In a Q&A session for Techrunch, CEO of Threadless said:

• It’s easy to burn through a lot of cash trying to figure your business out.
Bootstrapping (especially in a recession) has forced us to focus on what
works, and on gaining traction.

• The right time to make money is when you have something that works and
you want to blow it out of the water with explosive growth. Taking money
too early often hurts more than it helps, and looking back on our growth,
we believe that would have likely been the case with us.

• Focus hard and focus on your core. Almost anyone can make anything great
if they focus on it and dedicate their life to it. If all you did was think about
how to make one specific thing awesome every day, you would succeed.
Jake Nickell

• Entrepreneurism is glamorized and romanticized, but at


the end of the day, it’s really, really hard work, and it
requires a lot of sacrifice—not just from you, but from the
people around you. Make sure your friends and family are
ready to support you and then jump in. Don’t let the fear
keep you from doing it. You only live once, so if this is what
you’re passionate about, don’t have any regrets looking
back on your life. Just do it.
Aaqib Gadit
Aaqib Gadit
The Co-founder of Cloudways has said:

• As you would not need to go to any VC or Private Equity, you may end up being
the smartest person in the room (without BTDT) which is VERY dangerous.
Make sure to plug the outside wisdom from Advisors/Coaches as soon as you
reach 100K$ MRR.

• Being bootstrapped, the moment you are scaling (i.e validation, initial traction
has done) and having very good cash flows, you would try to balance your
personal risk (withdraw money for yourself) vs the re-investments you should
do in growth, people, research, etc. Make sure you don’t end up hurting the
business at the cost of your personal needs. Go with minor liquidity if this is
the case so you keep re-investing and stay healthy (both personal and
business)

• Remember John Doer’s quote: “ Entrepreneur does more than anyone thinks
possible with less than anyone thinks possible.”
Chris Wanstrath
Chris Wanstrath

The CEO and Co-Founder of GitHub said:

• Do it, but be smart about it. Use your brain. Think about
what makes the most sense for you. Worry about every
dollar you spend before (and even after) you’re profitable.
Focus on the things that matter and don’t waste time
endlessly redesigning your site or tinkering with new
technologies.
Larry Kim
Larry Kim
The CEO of MobileMonkey has said:

• Be (somewhat) delusional in your goals: When I created the business plan for my
first company, WordStream, I projected $26,000,000 in revenue in 5 years. 99%
of the candidates for hiring and investors looked at it and said: “this is crazy.”
Maybe 1% looked at the plan and were inspired. These are the believers — the
1% of people you need who can turn your crazy vision into a reality. In the end,
WordStream ended up beating my projection! The goal wasn’t even big enough!

• Find your unicorn growth hack: It’s a fact that 70% of your growth can be
attributed to the top 3% or 5% of your campaigns. A fraction of your blog posts
and social posts drive the most traffic and get the most engagement. You want to
look for those rare and remarkable opportunities that offer insanely high
conversion rates. Look to your past to find your unicorn growth hack. Everyone
has a unicorn.
Larry Kim

• Make unicorn babies: When you’ve found your


unicorn growth hack, replicate that same idea.
This may seem pretty obvious, but in my
experience, 95% of marketers favor new, unproven
ideas over tested, proven ideas. I think it’s totally
the wrong way of thinking. If something worked in
the past, it will probably work again in the future.
Make unicorn babies with your successful
unicorns. Be a Unicorn in a Sea of Donkeys!
Stephen Hart
Stephen Hart

The CEO of Cardswitcher said:


• I’ve worked with bootstrapped businesses in the past
and my current start-up, Cardswitcher, is a bootstrap
business. Here are three pieces of advice I swear by:
• Get in the right mindset: You might be a seasoned
entrepreneur, but I can assure you that setting up and
running a bootstrap company is completely different
from the conventional ones. It takes a very specific
mindset to succeed – a DIY attitude that combines
effective prioritization with exacting financial scrutiny.
Stephen Hart

• Obsessively track profitability: Unlike those businesses lucky enough to have


an angel investor or venture capitalist behind them, all of your capital is
going to come from what you can directly input yourself when you’re
bootstrapping. So you’re going to be acutely aware of getting as much bang
for your buck as possible. That means you need to keep very close track of
your overall profitability. After all, a bootstrap business needs to be
profitable right away or within a matter of months – not five years along the
line, like other businesses.

• Know when to ask for help: You can often develop a siege mentality when
you’re bootstrapping a business, just relying on your own resources and
ingenuity to solve challenges, but sometimes that won’t necessarily be
enough. Everyone needs help or advice occasionally, so don’t be afraid to
approach other friendly entrepreneurs or groups for advice about how to
solve particular problems. Your bootstrap will help you in the long term.
Bryan Johnson
Bryan Johnson
The Founder of Braintree, OS Fund & Kernel said:
• Bootstrapping is a force function for creativity and
breakthrough. It’ll challenge you to think outside the box
and to do things differently.
• In order to get the most out of bootstrapping, you need to
learn to become an expert in scarce resource utilization.
The key is to find clever ways to maximize the value of
every resource you have. It’s important that bootstrapping
be a tool in service of the objectives you care about the
most, not the objective itself. It takes constantly
questioning oneself to make sure these two are
continuously aligned.
Safwan Khan
Safwan Khan

The Founder of Startupily said:

• You need to have a kick-ass co-founder: If you are going to


bootstrap a business then you and your co-founder need to
be passionate about the business. Your skills should
complement each other. Focus on where your strengths lie
and work on what each person can do. If you or your co-
founder don’t have the drive, passion or work ethic of
making your business successful, then it will have a
negative impact on the business and you won’t go far.
Safwan Khan

• Promote, Promote, Promote your business: The only way for customers to
get to know about your business is by marketing and promoting it. You
should try all avenues of marketing to see what works and what doesn’t.
Scrap the strategies that don’t work and focus on what does. Try to get your
business out to the world as soon as possible. Speak to online blogs,
websites, media sites, PR to write articles about your business, create videos
and get featured on as many publications as you can. This will help you get
customers and will be good for marketing.

• Patience, passion, dedication and hard work: You need to be excited about
your business. Put in the hours, have patience as there will be times where
you would want to quit, but don’t. It takes time to build and grow a business.
Stop listening to people who say your idea won’t work because they are just
there to put you down. Believe in your abilities and just go for it.
Deborah Sweeney
Deborah Sweeney
The CEO of My Corporation said:

• Go into it prepared. When a business is bootstrapped, that means it is


completely self-funded. Figure out what your course of action will be
to finance the business, whether it’s through savings or using personal
credit cards, and what your strategy will be to budget and stick to that
plan.

• If you have any existing debt, pay it off in full before you begin
bootstrapping a startup. You will need every dollar you can get!

• Maintain a positive attitude. Bootstrapping means crunching every


possible number and sticking to a very tight budget. It can be difficult
to penny pinch this much day in and day out, so try to see the benefits
that bootstrapping ultimately provides your business in the long run.
Emmanuel Frost
Emmanuel Frost

The CEO of Brand Alignment said:

• The key to successful bootstrapping starts during the idea phase of the
company. If your business model is not built for low overhead, then you will
run out of personal financing very fast.

• Rather than hiring employees, pick shareholders that have jack-of-all-


trades skills. If you are starting an online business, then marketing and
programming experience is invaluable and will save a lot of money in
freelance costs and unnecessary ad spend.

• Experience. Experience. Experience. If you already know the lay of the land,
then you know which expenses to avoid, and which expenses they require.
Akshay Bansal
Akshay Bansal

The CEO of Heuro said:

• I think using the angel money might risk your company to


fail because of the many obvious reasons, but bootstrap
has to move very carefully because you might get only one
shot, so here is my advice:

• Save the arsenal: Try to budget the initial cash flow and
have some cash savings, it will tight your spending as well
as you will act creatively and have some arsenal for the
downtime.
Akshay Bansal

• Focus on early community and brand ambassadors of your


company: As AOL founder said in his book, The Third
Wave, now it’s all about the community, so make the
community and not the market.

• Delay the VC money: Like in the first point the more you
delay the VC money the better secession your company will
take. Once the big momentum starts driving your company
then you will have the cheap capital, which you can use for
the exponential growth of the company.
Natalie Athanasiadis
Natalie Athanasiadis

The Head of Growth, Ormi Media said:

• Try to spend as little as possible on costs that don’t generate a return


on investment (RoI). So for example, if you don’t NEED a new PC don’t
upgrade. Instead, invest in your marketing.

• Collaborating is a great way to grow your business when


bootstrapping. Can you skill swap or barter with another company?
Find ways in which you can be resourceful through collaboration.

• Be prepared to put in the elbow grease and put in the extra hours to
generate free publicity. It will cost you time, but it pays off for your
business.
Matthew Ross
Matthew Ross
The COO 0f Rizknows said:

• We raised a small angel investment in 2016 but other than


that we’ve completely bootstrapped our business. In my
mind, there are several advantages to bootstrapping a
business. First, the owners retain complete control over
the business, meaning they don’t have their hands tied by
investors or boards when it comes to major decisions.
Additionally, the owners retain 100% equity in the
business meaning they receive 100% of the profits and
100% of the proceeds if the business ever sells.
Matthew Ross

• Establish a litmus test: When bootstrapping a business, you have to


come up with a litmus test to determine what to spend money on
and what to ignore. For example, ask yourself whether the particular
investment in equipment or supplies is necessary to operate the
business? If the answer is yes, then spend the money. If the answer is
no, then ask whether the purchase will help the business grow? If
the answer is yes, then again spend the money. If the answer is once
again no, then you should probably hold onto the cash.

• Review financial statements on a monthly basis: You’ll want to keep


a close eye on your financials. As such, I’d recommend conducting a
financial review at the end of each month. This way you can gain a
better understanding of what expenses you can cut down and make
timely adjustments if needed .
Matthew Ross

• Hire slowly: Don’t feel pressured to run out and hire quickly. It’s okay to take your
time. I learned this lesson the hard way. In short, we needed to hire additional
employees very quickly over the past couple of years due to growth.
• The problem I ran into is that I was so focused on growing the company that I
didn’t take the time to properly vet and interview candidates. I just wanted to hire
as quickly as possible and plug them into the machine to keep the things moving.
However, after a couple of weeks, it was apparent that I had hired the wrong
candidates. Whether they didn’t possess the skills necessary to succeed in the
position or didn’t fit into the company’s culture from a personality standpoint.

• These hires actually hindered the company’s growth, which is quite ironic given I
was aiming for the exact opposite. Needless to say, I now take hiring and training
much more seriously, and spend a good amount of time vetting candidates, calling
their references and exploring their backgrounds to determine whether they’d be
a good fit.
Shel Horowitz
Shel Horowitz

Consultant & Media Guru of Transformpreneur said:

• Instead of squandering money on things like fancy offices and elegant


furniture, invest your resources in providing the best possible
experience with your product or service

• Start from the ground up, as a socially conscious company that uses its
products and services to address core issues like, how to turn hunger
and poverty into sufficiency, war into peace, and catastrophic climate
change into planetary balance

• Market that commitment–and market differently to different audiences


Hassan Al Nassir
Hassan Al Nassir
The CEO of Premium Joy said:
• Use Free Business Tools: As a bootstrapping startup, you should seize all
opportunities to use free tools for your business. For SEO and keyword
research, you can utilize Google Keyword Planner which is totally free rather
than throw money into a paid app like SEMrush or Ahrefs, which costs almost
$100 monthly.
• Utilize a Free Website Theme: If you want to reduce your startup costs while
setting up your business website, look into employing a free theme rather than
doing a custom design, as most popular web platforms (e.g. Shopify or
WordPress) do offer complementary templates which can be customized to
your liking.

• Learn How to do any Tasks Needed Yourself: Try as much as possible to learn
about all the tasks needed for your business to implement them yourself,
instead of hiring someone and paying money unnecessarily. You can find all the
knowledge necessary for running a business freely available online, whether
it’s about analyzing the market for opportunities, sourcing products from
overseas, setting up your company website, or doing internet marketing.
Ben Landers
Ben Landers
The CEO of Blue Corona said:

• Don’t run out of cash. You’ll make a lot of mistakes starting a company.
Your mistakes will help you learn the lessons from them. There’s only
one mistake you can’t make-don’t run out of cash!

• Your success or failure comes down to the early team. Hire people who
see problems as puzzles. Hire people who are really good at a lot of
different things and who are totally excited and bought into your vision
and mission.

• Build a marketing machine. One of the most important assets on your


path to viability is a marketing machine that generates new
customers/clients at an acceptable cost. In order to do this, you need
to adopt a mantra: track, test, tweak, repeat.
Michael Volosen
Michael Volosen
The of CEO, TeamUP said:

• Get specific with your product and service. Find where the gaps in the industry are,
and then identify the people who can use your product the most! The more specific of
a problem you can solve, the easier it is to find the right client or find someone who
knows that client.

• Make the calls yourself. It may terrify most business owners to actually pick up the
phone themselves and call their prospects. Use that to your advantage! While most
people are sending LinkedIn messages or emails, pick up the phone and call your
prospects and say you only want 15 minutes of their time.

• Talk to everyone. Tell the world what you’re doing. Go to local networking events,
knock on local business doors, tell all your friends, etc. The more people you talk to
and the more specific your product is, the more likely someone will remember you
and pass your contact information over.
Devashish Mamgain
Devashish Mamgain

The Co-founder of Kommunicate said:

• I have co-founded and successfully bootstrapped Applozic Inc.


and Kommunicate. I firmly believe that funding has killed more
startups than it has helped to grow but other than this thought,
my tips for bootstrapping entrepreneurs will be:

• Don’t hire for senior sales position such as VP of Sales: It will


only increase your burn rate as it will not bring in the value that
you perceived. At an early stage, you are the best person to sell
your product as no one knows it better than you. So be involved
in sales even if you are a techie.
Devashish Mamgain

• Value your Product and Team: Do not give your product for free
(unless you have a freemium model). You might come across
many startups who will play the startup card asking you to offer
your product for free. Don’t accept unless you get something in
return. If everyone starts giving their product for free. In the
end, there will be 0 customers and 0 revenue.

• Growth is the only KPI: Keep a track of your weekly growth rate.
As long as you are growing by 5-7% every week, you will
probably not need any external funding. Growth is the only
thing that matters and all your decisions should focus on growth
targets.
Laura Troyani
Laura Troyani

The CEO of Plan Beyond said:

• When we work with the founders of bootstrapped


businesses, we always make three core recommendations.

• Rather than bringing on full-time marketing employees,


consider leveraging a distributed workforce and
contractors as much as possible to keep overhead costs
low. This allows you to frugally test your way into
activities that will work for your business before bringing
in full-time staff to support them.
Laura Troyani
• Leverage your network to its fullest for new customer
acquisition. Do you know people who can use your
services? Do you know people with strong social media
followings who can talk about your business? Word-of-
mouth is an extremely effective and cost-efficient way to
build awareness and interest in your business. Use it!

• Make sure you always have a way to test the efficacy of any
marketing program you do. Building the right foundations
in your business so you can always measure and assess
how effective your marketing campaigns are, is the only
way to know if you’re spending your marketing budget
wisely.
Tyler Rooney
Tyler Rooney
The Co-founder of Format said:
Being a bootstrapped startup founder, I can understand. My three points for
aspiring startup founders are:

• Get a good co-founder: There’s too much to do and literally no money so make
sure you find a good partner. It will be a long time before you have people in
dedicated roles, so find someone who is well rounded and isn’t afraid or too
proud to do any job. Ideally, find someone who enjoys doing the jobs you hate.

• Develop financial discipline: personally and professionally. If you’re


bootstrapping a startup you’re going to need savings and financial discipline.
You live and die by your cash flow so make sure you can deal with both
emergencies and sudden opportunities. Missing on either of these can deal a
fatal blow. The flip side of this is learning when you’re wasting money or
missing an opportunity by not hiring someone, not outsourcing certain tasks,
or using some cheaper alternative instead of the tool you actually need. Make
sure you’re investing for success instead of just survival.
Tyler Rooney

• Never forget your customer: Your early customers are the


most precious asset you have. Not only are they your
source of revenue, but they’re the source of essential
feedback and, hopefully, they’ll be your first evangelists.
Make sure you’re always listening to them, being of service
to them, and being real with them. Getting this right can
really prime the pump on multiple fronts.
Ande Lyons
Ande Lyons

The CEO of Startup Life said:

• With four businesses to my credit, I know from personal


experience how to launch, brand and build a business without
spending a lot of money, or wasting a lot of time.

• If you have an accelerator program in your community,


preferably a non-profit/free program – apply to it. Accelerator
programs provide training to newbie founders, provide
mentors to give you much-needed advice and feedback, provide
a structured setting to help founders focus on their business
and a support system with other business founders.
Ande Lyons

• Enter pitch competitions. It is the best exercise to prepare a


founder to speak clearly and succinctly in front of a crowd about his
or her business model and value proposition. Pitches provide free
advice and expert feedback from seasoned entrepreneurs and
investors; an opportunity to increase brand awareness; you can win
money and/or complimentary services; networking at the event
can create introductions and open doors to secure new hires,
attorneys, seed funding, etc.

• Hire a bookkeeper! Founders are strapped for time and need to


carefully manage cash flow. The bookkeeper can take care of
payroll, taxes, and provide the most important tool for a business
owner: a monthly cash flow statement.
Sherman Lee
Sherman Lee

The CEO of Raven Protocol said:

• I’m a serial entrepreneur who has both bootstrapped businesses and raised funding.
There’s an unspoken sign of respect when you meet someone who is bootstrapping.

• Be proud of bootstrapping: If you can get through this, with minimal resources, you
will be successful. This is infinitely harder than having the cash to solve your problems.

• Define what success means to you: It’s easy to blur your vision with the Techcrunch
stories of another company in your space raising $80M. You start to question yourself.
Should you have raised money? Having an internal metric for success means you can
be happy about your accomplishments.

• Reinvest in your business: Since you never raised any funding, cash is always tight. Use
your revenues wisely. It will pay off long-term.

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