I’m shutting down SoHelpful — what I learned from helping 10,000 entrepreneurs

Kevin Dewalt
Actionable AI
Published in
13 min readOct 3, 2016

At the end of October I’ll be shutting down SoHelpful, a SaaS startup I’ve been running for 3 years. More than 10,000 Startup founders have given and received advice on SoHelpful. The friends and colleagues I met through SoHelpful have changed my life.

Helping founders started as a habit … then became a side project … and ultimately a small business. Growth was 100% organic and SoHelpful was profitable from day 1 with no outside funding. But I never found a way to turn it into a growth company so it’s time to declare a small victory and move on.

Below I present my unabridged SoHelpful experience, the good and the bad. It’s a story of … an American entrepreneur in China? … someone who built an amazing network helping others over Skype? … a side project that took on a life of it’s own?

TBH I’m not sure. I guess it’s just my story. I hope you find it enriching.

A lonely Laowai founder in Beijing

In 2012 I moved to Beijing, China. I spent a year getting settled, learning Chinese and helping new programs like Chinaccelerator and JFDI. I founded Beijing Lean Startup Meetup and organized the first Startup NEXT program in China. I met tons of founders, other Angels, and invested in Vericant and Collabspot. But by 2013 I was getting the itch to work on another startup — but what?

Beijing Lean Startup Meetup. Can pollution stop us? No way!

I was only going to be in China for a few years so doing a startup for the Chinese market was out. I wanted to work with Western entrepreneurs and build something for the startup “market” (more on this later). Unfortunately Beijing doesn’t have a startup community as we think of it in the US. Turnover is extremely high and there were only handful of entrepreneurs like me.

China can be lonely for founders serving a Western market. Sometimes 包子 (Bao Zi) was my only company!

So there I was … sitting in my Beijing apartment … with my cat … wondering how I was going to meet more Western startup founders.

Joel Gascoigne inspires me to make helpful a habit

My most valuable startup relationships happened by helping people work through problems. I never tried to engineer these opportunities — they just sort of happened. But what if I made helpful a habit? Could I begin building relationships with entrepreneurs worldwide by helping them over Skype calls? Fortunately I have a friend who was doing just that — Joel Gascoigne of Buffer. So I asked Joel about his experiences helping fellow founders.

Joel Gascoigne of Buffer gave me some great advice about helping startup founders.

We talked about his experiences — how to help founders, schedule calls, deal with cancellations, etc.

I decided to give it a shot.

I created a page with a few sentences about my offer to help entrepreneurs and a link to a Google Appointments (now shut down) scheduler.

My biggest concerns were:

  • Too many calls
  • People calling to sell me stuff
  • Founders calling to pitch me for money

I promoted my offer on social media and my mailing list and waited for the deluge.

… and nothing happened. Nobody called me for help.

Hundreds of people were coming to my landing page and NOBODY booked a call with me! Sure a few friends called to “catch up” but I wasn’t meeting anyone new.

I was pretty surprised since founders were asking me for coffee meetings, calls and advice. Something was wrong in my execution.

I decided to make my offer more attractive by:

  • Putting up a picture of myself
  • Listed specific topics we would cover in a call
  • Adding testimonials from friends
Nobody would schedule time for help until I created a landing page with a value proposition

It worked!

Slowly things started changing and founders began scheduling calls with me. I was meeting awesome people worldwide and getting better about helping them through. At first I prepared for the calls by researching the founders and their problems. But this wasn’t necessary because they just needed someone to listen, clarify, and help them see options.

I started creating scripts and templates to manage the workflow. At the end of each call I asked founders for a quick testimonial and to tell others about it on social media. More calls started coming in and soon every slot filled up. I did no preparation and worked right up to the point when the call started.

Surprise! The smartest people ask for help

My biggest surprised was in WHO scheduled time with me for help.

I had worried about wasting time with opportunistic/lazy founders. In reality the best were drawn to my offer.

Many were living in areas without a startup ecosystem. It was obvious why I had to convince them to schedule calls with me — these were busy, talented, smart people who had choices.

The conversations were different than the usual “meet me for coffee” chats. Anyone can ask for a coffee meeting or show up at a Meetup. The people who scheduled calls were trying to solve problems and not engaging in dreamy chit-chat.

I started meeting amazing founders worldwide. A simple testimonial was the best thanks in the world.

Results — the good and the bad

The experiment worked far better than I could have expected. NOBODY ever tried to sell me anything or ask for money, but of course it wasn’t all roses and sunshine. My scheduled calls broke down into roughly 3 buckets:

  • ~30% were no-shows or failures due to technical issues.
  • ~50% were good conversations.
  • ~20% were amazing — new life-changing relationships.

The process was efficient. I let anyone book a call so there was no upfront work. Since I worked until the call started I wasn’t bothered by no-shows — I just kept working. I blocked out 30 minutes for the calls and the actual talk time was about 20 minutes. I found myself skipping generic Meetups and coffee meetings because my startup help calls were so much more efficient.

Being helpful is an OPPORTUNITY — and like all opportunities it takes work to create them.

Marching to 1,000 True Fans

After just 30 calls my audience was growing. The people I helped became my biggest supporters and helped promote my work on social media. After 50 calls I was seeing the beginning signs of becoming famous.

Most people I helped left me testimonials and told others about me. After just a few months I was on my way to becoming famous.

Accelerators called me looking for mentors and conferences asked me to speak. Unsolicited consulting opportunities started arriving.

Dave Haeffner referred me to Kevin Kelley’s famous essay 1,000 True Fans. I realized how I could become famous — keep doing startup help calls until I helped 1,000 people.

At scale I could have 5–10 30-minute startup help calls every week.

At this rate it would take me 2–3 years to create 1,000 True Fans and achieve some level of fame.

SoHelpful is born — a habit turns into a business

Calls were great but scheduling sucked

Talking to founders was great. Scheduling calls … dealing with reminders … contact info … time zones … follow-up requests for testimonials … it all started to get old after a few months. I couldn’t find the right scheduling system: Google Appointments shut down, RIM scuttled Tungle, and the remaining options like YouCanBookMe and ScheduleOne didn’t have the workflow I wanted.

Building a drop-dead simple scheduler was my biggest challenge

Asking for testimonials and spreading the word on social media became too tedious. I started a side project to build my own tool to manage my startup help calls. It saved me a few hours a week.

Automating the testimonials and social promotion saved a ton of time

I now had my workflow hacked. Scheduling, testimonials, social media sharing … it all worked seamlessly and I could invest my time talking to founders.

Friends wanted to pay me for my help-startup tool

I started showing my “startup-help-call-scheduling-tool” to friends helping founders over “office hours”. A few asked me to create one for them. I said … forget it! Go make your own. My hacked-together scripts were fine for me but hardly ready for prime time.

Then they asked me a question that got my attention: “Would you build one for me if I pay you?”

I’m not the world’s smartest entrepreneur, but when I’ve built a tool I love and others offer to pay for it … well … it gets my attention.

MVP and problem-solution fit

I called the system “SoHelpful” and charged $9/mo. The MVP had only a few features:

  • Profile with help offer
  • Call scheduling with Google Calendar
  • Testimonial workflow
  • Reminders & contact info

It took a few months to work out the kinks and I slowly started getting customers and growing ~10%/week. Growth was 100% viral — someone would book a call on the platform, have a good experience, and then sign up.

$1K in MRR

After about 6 months my SoHelpful side project was becoming a full-time job. I hit $1K of MRR with 0 marketing. I hired Joey Mendoza and Chiara Cokieng to help me out. I was living in Beijing and building a team in the Philippines was ideal since we were in the same time zone and I was a direct flight away.

The (failed) search for Product-Market fit

An initial core group of amazing customers

Up to this point I didn’t have a vision. What started as a fun side project was becoming a job. Most of my early customers were having a similar experience as mine — they were building amazing new relationships worldwide. Getting early customers for their products. Growing their social media presence. Getting new consulting engagements.

The feedback from these early customers was unbelievable — they had an emotional connection to SoHelpful like few products I had seen.

Most had a small audience through their blog and used SoHelpful to build closer relationships with them. All were helping founders before using SoHelpful. We started having Hangouts together to share best practices.

Scaling challenges: “Nobody called me”

Unfortunately I started seeing problems when we passed 100 paying subscribers. People started signing up for SoHelpful who didn’t have an existing audience. Aspiring coaches. Authors. Freelancers.

Most had calls with someone else on SoHelpful, had a great experience and wanted to help others. They would sign up and cancel after a month or so when nobody booked a call with them.

I hit the dreaded SaaS brick wall: churn.

Info products? Not for me

I tried to overcome this problem by teaching other entrepreneurs to do “Helpful Marketing” as I was now calling it. Gary Vaynerchuk was one of my inspirations. I started creating courses and books to teach other entrepreneurs how to do it. I briefly considered making a career out of becoming a business guru.

I captured my experiences in my first book Get Your 1st 100 Customers.

I captured everything I learned about Helpful Marketing in my ebooks and courses. Unfortunately others just had a hard time copying my success. I wanted to do more than just make money and promises.

I met my first goal of selling 99 copies at $39.99 in just a few weeks — mostly because we had an email list from people who took our free course. And the hundreds of people I helped over Skype calls promoted the hell out of it.

These are good results for a first-time author but I wasn’t happy with the impact. Most people were looking for an easy button and didn’t have the interest/time/ability to market themselves. Sure, they would buy my book and sign up for SoHelpful. But they didn’t get calls, gave up, and churned.

Beyond that I wasn’t interested becoming another startup “guru” selling info products (more below). Startups are about making a big impact — otherwise it just isn’t worth it to me.

I decided to leave this mission to Gary Vaynerchuk and move on.

Danger: A general tool for a general problem

In spite of these challenges SoHelpful grew organically each month. Most customers were looking for a general scheduling tool and liked SoHelpful’s simple workflow, widgets, and mobile interface. Others wanted to join a “community” and booked calls with others on SoHelpful to give and get advice. Still others were SaaS customer success teams using SoHelpful to do onboarding calls with new customers.

This was a big problem — you can’t build a business if you can’t solve a specific customer problem. We needed to focus to hit product-market fit.

SoHelpful was on a trajectory of becoming a small lifestyle business. This was an outcome that didn’t interest me, particularly since the core market seemed to be coaches and freelancers. I decided to try and pivot to a bigger opportunity or do something else.

“Scheduling tools” are shitty businesses

The most obvious opportunity would be to do what most customers were asking us to do — build a better “scheduling tool”. I ruled out this option because I just didn’t see a way to build anything other than a small lifestyle business. RIM, Google, and a host of other big companies had tried and exited the space. I didn’t want to join the graveyard of mediocre, low-margin products in the market.

Sometimes the best choice is NOT doing what customers want you to do.

(No offense meant to anyone working on this problem — just my opinion, YMMV.)

Nobody pays for phone calls

Other customers encouraged us to create an “expert” network where startups would pay for advice. I also ruled out this option as well. I’ve watched companies try to create expert networks since 1997.

People won’t pay for phone calls — well, except for 1–900 numbers and psychic readings.

I did customer development on Clarity and Google Helpouts and didn’t see any evidence to change my mind. Unless I built a network like GLG and sold advice services to private equity fund managers I didn’t see an opportunity.

Beyond that … getting paid for advice just didn’t interest me. I liked the relationship-building part of meeting other founders on my startup help calls. It felt like a meeting between smart colleagues trying to solve a problem together. These relationships were 1000x more valuable than any money I could earn charging for phone calls.

Concierge onboarding sounded good … but …

I did find one potential use case. Several customers were using SoHelpful to schedule onboarding calls with trial customers. SoHelpful’s simple scheduling and testimonials increased the number of customer calls … which lead to more sales.

I spent a few months doing Customer Development on concierge onboarding and received a lot of positive feedback. Everyone liked SoHelpful’s scheduling workflow with custom branding and CRM integration.

I tested a pivot to All Aboard! — a standalone concierge onboarding platform. We got ~10 paying customers but had a difficult time getting them to use it. Why? They didn’t want to look at another screen with the same customer data.

Customer Development works well to validate a problem — but validating a solution requires giving customers an experience.

I didn’t see a bigger opportunity and decided to pull the plug on All Aboard! a year ago.

Calling it quits

By this time I had moved back to the US and was ready to do something else. SoHelpful was on autopilot so I decided to support it for another year — largely because I was still using it.

But that year is up and it is time to move on.

Lessons Learned

I got a 10x return on my investment helping startups

The calls generated new colleagues, advisers, customers, and investment opportunities. I truly did get 10x back from it.

I met the MadKudu founders over a startup help call. I ultimately became an investor and interim CMO. And I made lifelong friends with this amazing team.

A big factor were the testimonials on my SoHelpful profile. People had just never seen anything like it. No “About me” page, LinkedIn profile or resume compares with showing how much you impact people on a personal level.

… but part of my success was timing

I started helping founders just before incubators, accelerators and educational programs exploded worldwide. Founders wanted to connect and get basic feedback on their businesses.

Today the most capable people can turn to local resources for this help. I’m not sure the same approach would be as successful today.

Were I to do it again today I would focus on a narrow, underserved niche — founders over 60, women in tech, etc.

I wish I had Bootstrapped a startup earlier in my career

I had raised institutional money from VCs or grants for every previous startup. In retrospect I learned more about business by bootstrapping as a single founder.

By spending my own money I was forced to confront the real issues from day 0. I am a better entrepreneur as a result.

Sometimes startups just don’t work out

Looking back I don’t see a point where I made a big blunder. Before we hit 100 paying customers the feedback was unbelievable.

“You changed my life!”
“I got 2 consulting gigs from SoHelpful — this is worth 100x what I paid for it.”
“No trial customers booked time when I used a generic scheduler — the testimonials on our SoHelpful profiles changed everything.”

It is tough to build something which creates such an emotional connection with customers. I’ve seen it only a few times in my career. I tried to build off of this initial traction but never discovered a big enough opportunity.

Sometimes it just doesn’t happen.

The startup “market” is an education play — and it has a creepy side

Ever notice a “make $1,000/month from home” paper flyer at an intersection? That’s the big market for “entrepreneurs”. You can package it differently or write compelling books but the human need is the same: people looking for an easy answer. So they’ll pay a small bit of money in the vain hope some new guru has it.

This is purely a personal choice — I wasn’t excited about building this type of business. Helping startups worked amazing for me but I didn’t believe the larger market could replicate my success.

Of course there are exceptions like Ash Maurya and Gary Vaynerchuk. They give great advice and guarantee nothing without years of hard work.

Thank you!

I’ve met thousands of people through SoHelpful and can’t possibly thank everyone. So I’m going to give a personal shout-out for the people who helped me get it off the ground in the first year.

Thanks Chiara Cokieng and Joey Mendoza for making SoHelpful a great product.

Thank you Mike Fishbein, David Schneider, Shane Walker, Dave Haeffner, Bruce McCarthy, Spike Morelli, Paul Mederos, Grace Ng, Brian Jordan, Ramli John, Andrew Culver, Justin Wilcox, Teague Hopkins, Shardul Mehta, Dan Siegel, Jonathan Leow, Shane Reiser, Mark Horoszowski.

My apologies to the thousands of amazing people I left off this list.

So … what’s next for me?

AI has been a passion since I did my graduate work at Stanford in the mid-1990s on neural networks. More than 20 years later that technology is finally making real business impacts.

I decided to take a break from startup products to help bigger companies develop AI strategies and generate new revenue streams from machine learning.

You can reach me at kevin@484labshq.com.

--

--

Kevin Dewalt
Actionable AI

Founder of Prolego. Building the next generation of Enterprise AGI.