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My First [Big] Web Design Pitch was a Complete Failure

I started making websites in 1997. I received money for the first time in 1999.

From 2000 to 2004 I was going to university, but working with Steve Thiel in my spare time to build website projects. We were doing website builds full-time from 2005 to when we sold our agency in 2012.

During this time, we created hundreds of sites, receiving millions of unique visitors.

I have a lot of great stories from these years, but I want to share with you my first big failure.

It was the summer of ‘04. I was young, ambitious, and knew a thing or two about web design.

At the time, our business was called Crystal Clear Designs. In retrospect, we had our pick of the litter when it came to domain names related to web design, but for some reason we chose that behemoth.

Eventually we changed our name to HotPress Web because people thought we were a window cleaning company. Different story entirely.

I (already) digress.

The client opportunity before us was the California Coalition Against Sexual Assault (CALCASA), a nationally leading nonprofit organization aimed at the movement to end sexual violence.

Up until this opportunity, we got paid a couple thousand dollars per project. CALCASA had a high five to six-figure budget.

A friend of ours worked at the organization and assured us we were a shoe-in for the business. We just needed to nail the proposal and pitch.

Request for proposal (RFP) in hand.

Time to win big.

Kick start our side business into a full-time operation.

Spoiler alert: we failed…miserably.

Not only did we not get the business, but it was awarded to another company for a lot more money than our offer.

I was crushed. Luckily, after we got the bad news, we grabbed two bottles of Johnny Black and decided we wanted to keep doing this.

But before we get into that, let’s dig into what happened.

My Contact

A close friend of mine worked at CALCASA. He reached out to me and let me know he had a great opportunity for us.

He knew our work pretty well and knew we could handle the project.

All we had to do was show up to get the business.

Mistake #1: Even though he was not the final decision maker, I spent the majority of my time communicating with him.

There was a panel of stakeholders that was involved in the project. The organization, at some level, wanted to keep them out of the process to make sure their time was best used.

I shouldn’t have stood for that.

Getting access to every stakeholder is the only way to proceed.

RFPs Are False Alarms

CALCASA painstakingly spent weeks creating an RFP that had all of their requirements wrapped up in a nice little bun.

We were sent the RFP.

The document outlined some basic requirements:

  • New design
  • Content management system
  • Content-centric
  • Multilingual
  • Rape crisis center directory
  • Accessible content
  • Tie into their existing database system
  • Use indexable terms for search

Surprisingly, this set of requirements is still pretty typical today for nonprofits.

I read the RFP and my brain went directly to: “can we do this?”

I analyzed the functionality and came up with a plan to accomplish what they asked for. I kept this practice for a long time: client sends RFP, I submit proposal for that RFP.

What I didn’t understand at the time was an RFP is simply a client writing out their perceived requirements.

Mistake #2: I thought an RFP was just what it says it is – Request for Proposal.

It’s not.

Proposal happens after discovery…and clients are not equipped to do their own discovery.

RFPs are a call for help. It means that an organization or company has identified that they have a problem. And they’d like you to help solve it for them.

Imagine going into a doctor’s office and saying: “Doc, I got a real bad headache, I know it’s cancer, so let’s go ahead and get me hooked up to that chemo and get this over with.”


But in web this practice is extraordinarily common.

Clients just want to get a stack of proposals and then pick who is right for them. Web designers like to send out as many proposals as possible.

It took me years to learn that RFPs are truly RFDs: Request for Discovery.

My Heart’s in this Proposal

Armed with the RFP, and my friend on the inside, I was ready to craft a proposal. Mind you, I had not talked to any other stakeholders at CALCASA, but that didn’t matter, I had the RFP (meant to be read with extreme sarcasm).

I called a couple of friend’s parents that I knew who were in sales and asked them what should be in a proposal. I came up with this basic outline:

(Never use this as your proposal structure.)

  • Cover page (w/ our logo)
  • Second cover page (w/ their logo)
  • Contents
  • Background
  • Team
  • Our plan
  • Project timeline
  • Project cost
  • Addendum
  • Portfolio
  • References
  • Contact information

As you can see from the worst website proposal I have ever crafted, I poured my emotions into the very first section.

To give myself an ultra hard time, I would like to call out this sentence: “and make your organization part of our life’s accomplishments.”

All in baby.

Mistake #3: I didn’t talk about the client or their problems until page seven.

It was all about us and why we are so great.

Besides the overall structure being problematic, my actual writing style and formatting were amateur. I was used to writing essays in college and looked at a proposal through that lens.

I didn’t understand brevity wins. I didn’t know how to write a proper scope of work. Problems, objectives, solutions, and terms were not part of my vocabulary.

I crafted a timeline when I really didn’t understand the client’s buying process or even know with whom we’d be interacting on their end.

It’s okay to use an amount of time when giving an early estimate, like “two weeks” or “one month,” but to define a specific calendar date is irresponsible. It doesn’t matter if the client wants specifics.

My addendum is what blows me away though.

Two-year maintenance and system improvements at 50 hours per month for $15,000.

$12.50 an hour. I’m thinking I didn’t own a calculator at the time.

Since we knew the person helping to facilitate the process on CALCASA’s side, we got invited to pitch in person.

Pitch Time … Shark[ette] Tank Anyone?

Steve and I used what little money we were making in our business to get a couple of plane tickets to Sacramento. This was our big break and we were excited.

We stayed at our friend’s house and turned his kitchen into a war room. He even gave us the questions the stakeholders were going to present to us the next day. We figured: “if we can nail the answers to these questions then we are golden.”

I cringe at so many parts of this story …

We literally “studied” the questions and our presentation as if we were doing it for school. Granted, we were coming directly out of university, but the whole exercise was fraught with failure.

CALCASA had set up a couple-hour block with about eight of their staff to sit in on the meeting. Thinking back to the whole process, it was really crazy. We let them lead the entire show.

I had only seen business pitches on TV. This was before Shark Tank…so think Glengarry Glen Ross or Boiler Room.

I had never even been in a real conference room.

On pitch day, our chosen attire were black suits. I wore a tie and Steve did not.

Mind you, this is a nonprofit based in Northern California and run primarily by women. I’m not saying suits and ties are bad…but for this particular instance, we looked like we didn’t have any clue who we were pitching to.

And to be fair, we didn’t.

We showed up on time and were let into the conference room to set up.

What followed has been etched in my brain forever.

We chose to stay standing as everyone came into the room (seven women and our friend, who was a guy). A ball was tossed from person to person to introduce themselves. It was as awkward as it sounds.

After that was all done, Steve and I started our presentation.

Just dug right in.

Slide after slide, explaining to this room of people whom we didn’t know, about the system we were going to create for them and how great it was going to be.

After that we sat down and they asked us all of the questions we had already rehearsed answers to.

I’m not sure either of us asked one question during the whole meeting.

At one point, I looked across from me and one of the women was actually falling asleep. She was so disinterested in what we had to say that she was sleeping at the conference table. It blew me away.

Mistake #4: I spent the whole time pitching and not conversing. There was no discussion about pains and needs and frustrations. There was no discovering.

Even still, I figured we were crushing it.

Mistake #5: I prepared too much about the stuff that didn’t really matter. I figured it was all about our solution, based on their RFP.

I should have researched every CASA in the country and other top nonprofits that I thought had similar problems. I should have spent the whole time digging into their problems to discover what truly mattered to each person in the room.

After a couple of hours, we left their offices and headed off to celebrate.

In our minds, we nailed this.

Celebrating a Tad Early

Instead of looking at this bid as a simple opportunity, it was our big break. I didn’t understand that even if we had known what we were doing, we might not have won it. There are so many unknown factors.

Emotionally, we put our all into this and we were convinced we cinched it.

Steve and I left their headquarters in the early afternoon and went and grabbed a late lunch. We had some drinks to celebrate our soon-to-be victory.

Champagne toast to be exact.

On the way back to our friend’s place, we picked up a bottle of Johnny Walker Black to keep the party going. About halfway through the bottle, our friend got home.

The look on his face was ghastly. It was immediately obvious that it didn’t go as planned.

“It’s done. No chance.”

Mistake #6: We counted our eggs before they hatched. Celebrate when you have a check in your hand, not when you finish a pitch.

Apparently what transpired after we left was a four-hour discussion. Our friend was batting for us the whole way. With only one interaction with us, the seven women did not approve.

They didn’t understand anything we were saying about CMS, databases, permissions, roles, content workflow, security, speed, or anything else.

All they saw was two guys that looked like they were on their way to the club (apparently that’s what black suits mean in California). One girl actually said, “They look like some dudes at a Miami club.”

Because our presentation was anchored in what we thought was important based on their RFP, and not on each team member’s specific pains, nothing we said sunk in.

I probably would have fallen asleep too.

Second Bottle of Johnny Black

After talking over the situation from every direction possible, our fate finally sunk in. Our big break was over. We got smoked.

Steve and I did the only thing we knew to do: got a second bottle of scotch.

The three of us drowned our sorrows while discussing: what could we have done differently?

Our system? Our attire? Our proposal? Our price?

It would take me years of experience before I would be able to properly answer that question…

It was everything. All of the above. We screwed up each and every portion of the entire opportunity.

The only thing that brings a smile to my face when thinking about this story is what happened next.

Half way down bottle #2 of JWB a euphoric exclamation was made. Steve and I were on our friend’s patio (our friend was passed out in the bathroom) talking business future. We both enjoyed Marlboro 27’s at the time.

[Set scene: smoke pilfering from the patio, scotch voices in full pitch, arms waving, rocks glasses in hand.]

“What if we did this for a living?”

“You mean like instead of getting real jobs?”

“Yeah, like we just kept building sites and stayed the course with web, made a real business of it.”

“I think you might be onto something.”

“You should move out to Colorado after school, and we’ll live in my parents condo and get ourselves up and running.”

“Let’s do it.”

[End scene.]

Following this conversation, we ended up going out with some of our friend’s mates from the area. It ended up being a pretty crazy night.

To this day, there is a small group of people that live in Sacramento who are wondering if we’ll ever come back for a second round.

Think Long Term
Funny turn of events. After we lost the business for the website revamp, CALCASA actually hired us to provide their web hosting.

We ended up keeping them as a hosting client for about four years—long enough to get in with several other California nonprofits and government clients that are still HotPress Web clients today.

Ultimately we got fired because of the Great Server Crash of 2008, but that’s a story for a different day.

Even though we completely butchered ourselves on the proposal and pitch, the door stayed open. Several of the women that were in the room that turned us down got to know us and our service abilities. They referred us out and continued to work with us as they moved on to other jobs.

There are many lessons you can take from this story, but I will close with my favorite two words: patience & perseverance.

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