Writing a winning proposal

We’re big fans of Ran Segall and Flux Academy, an online learning platform for freelance web designers. We only recently discovered that he started (and later sold) Prospero, a nifty tool for creating business proposals — so he’s an expert on this topic. Below is an overview of Ran’s top tips for writing a winning proposal; see the entire presentation here.

The goal of a winning proposal:

• Summarize your conversation & align expectations
• Make the client trust you
• Make the price look reasonable
• Make the client sign it

Things to remember:

• Keep it short (people hate legal docs).
• Sell yourself.
• Have a clear CTA (call to action).
• Write like you speak.

What to include in a proposal:

• Overview: Show the client that you REALLY understand their problem and why they need your help.
• Why Me: Your client will be getting other proposals, so make sure it’s very clear why working with you is best.
• Process & Cost: You are selling a process and not a product. Tell them everything that’s going to happen to make the investment reasonable.
• What’s Next: Add a clear call to action with next steps — how can they get started? What happens next?
• Terms: How you communicate and charge; what’s included/not included.

Our take:

The internet can be an endless rabbit hole — there is so much information. We found Ran on YouTube and that can be the best starting point when researching “how to’s” and other queries. As for writing good proposals, Ran’s direction has proven to be successful for us. You don’t have to come up with every “best” solution yourself or do everything alone!

5 lessons we’ve learned about owning a small business

1. Work with the right partner and hire the right people. We learned this one the hard way years ago — sitting in mediation with a litigious third partner (and former friend) in our first business. It was a painful process, but we continued on and discovered our two-person partnership was much stronger than the original. (And we’re still together.) As for hiring, we learned it’s better to hire one “right” person and pay them more than to hire several “wrong” people and pay them less. Rachel is an indispensable part of our team — and guess what, she also worked for us in business #1. But that’s a story for another day…
   
2. Don’t overextend yourself personally to cover business expenses. It’s the rare entrepreneur who doesn’t put some personal funds into the business, especially in the early days. But if income from your work consistently doesn’t cover the expenses of doing the work, it’s time to do something else. In hindsight, we would have closed business #1 sooner.
   
3. Be intentional about maintaining a strong work-life balance. Many people dream of the “freedom” they’ll have by becoming their own boss. In fact, it’s likely you will work harder and dedicate infinitely more hours than any job you’ve had when working for someone else. Maintaining a healthy work-life balance is essential to going the distance. This means keeping manageable office hours (even if working at home), taking time off, delegating, and paying attention to your body, mind, and spirit (not just the bank account).‍
4. Charge what your product or service is worth. I wish we had a dollar for every pricing debate we’ve had through the years. Are we charging too much? Not enough? It’s even harder when your “product” is a service. There are lots of factors to consider. What does it cost to stay in business — and make a profit? What experience and expertise do you have that sets you apart? What is the value to the customer? In the end, pricing requires some experimentation to find the sweet spot.‍
5. Focus on your strengths, stay nimble and never stop learning. Our current business looks very different than it did when we started. In the early days, we did pretty much anything someone needed, whether we enjoyed it or not, even if it wasn’t very profitable. For us, the pandemic offered an opportunity to make some important changes. We had time to think about what was working and what wasn’t. We’ve written on this topic in other newsletters — how we navigated the slowdown in 2020, upgraded branding and services, signed up for online classes, etc. Now we’re more excited about our work than we’ve been in a long time. A good place to be.

Stories from a round table

My proudest possession is a round oak table — originally my grandfather Elmer’s poker table, passed down to my father, then to me. When Elmer hosted “Hots” Tingle and other friends for basement card games, the table was black. Later, Dad stripped the paint and lovingly brought the oak back to its original glory. It stood proudly in my parents’ kitchen for years, the center of countless meals, celebrations, conversations, games, and craft projects. Every scratch and imperfection is a memory.

A round table has no corners, so everyone belongs. It’s where friends and strangers were welcomed into our family. When the whole gang came to town for holidays, it’s where Mom laid out a spectacular buffet — and where we held hands and stood in a circle while Dad prayed a very. long. prayer. (He was a preacher who loved to talk — to God or anyone.)

Eventually my parents downsized to an apartment and the table came to me. It was a tight fit in the former one-room schoolhouse, but we were happy to continue hosting family gatherings for several years. When we moved to Portland, we watched as the table was disassembled, carefully wrapped in blankets, and stowed in the moving van. We drove behind the truck for 2,700+ miles through frosty plains and snowy mountain passes. When we unwrapped the table, it had few more dings — but so did we. It looked perfect.

Dad never got to see the round table in its new home. He died peacefully in his sleep last year. In June, we buried his ashes in Kentucky, a few miles from the house where Elmer hosted his poker pals. I’d give anything to hear one of Dad’s sweet prayers and share another family meal at the round table. Mom just celebrated her 90th birthday and she hopes to visit us next Spring. We can’t wait for her to pull up a chair in our dining room.

The round table has come a long way. We love hosting meals and Chicken Foot games with our west coast family. When it’s safe to gather, we look forward to welcoming friends for dinners and holidays. And guess what? Our neighbor is a professional poker player, so we might even learn some new tips. Elmer would be happy. The tradition continues.

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